n-Butyric acid by Asch

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Date

804 reactions in Reaxys

2017-08-01 04h:34m:41s (EST)

1. Query OH

Search as: As drawn, No mixtures 2. Query

(1. Query) AND itemno in (1,2,5,6,7,8,9,10,13,15)

804 reactions in Reaxys

2017-08-01 04h:38m:02s (EST)

3. Query

(2. Query) AND itemno in (1)

804 reactions in Reaxys

2017-08-01 04h:39m:41s (EST)

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O O

Rx-ID: 645848 View in Reaxys 1/804 Yield 100 %

Conditions & References With 2,2,2-trichloroethylperoxycarbonic acid, dihydrogen peroxide in dichloromethane, Ambient temperature Tsunokawa, Youko; Iwasaki, Shigeo; Okuda, Shigenobu; Chemical and Pharmaceutical Bulletin; vol. 31; nb. 12; (1983); p. 4578 - 4581 View in Reaxys

99 %

With C4H11FeMo6NO24 (3-)*3C16H36N(1+), water, oxygen, sodium carbonate, Time= 8h, T= 50 °C , p= 760.051Torr , Green chemistry Yu, Han; Ru, Shi; Dai, Guoyong; Zhai, Yongyan; Lin, Hualin; Han, Sheng; Wei, Yongge; Angewandte Chemie International Edition; vol. 56; nb. 14; (2017); p. 3867 - 3871; Angew. Chem.; vol. 129; nb. 14; (2017); p. 3925 3929,5 View in Reaxys

92 %

With (bipyH2)-CrOCl5 in dichloromethane, Time= 0.5h, T= 28 - 30 °C , oxidation with further chromium reagents Chakraborty, T.K.; Chandrasekaran, S.; Synthetic Communications; vol. 10; nb. 12; (1980); p. 951 - 956 View in Reaxys

92 %

With tert.-butylhydroperoxide in water, Time= 2h, T= 70 °C , Green chemistry Sodhi, Ravinderpal Kour; Paul, Satya; Clark; Green Chemistry; vol. 14; nb. 6; (2012); p. 1649 - 1656 View in Reaxys

89 %

With tert.-butylhydroperoxide, copper(ll) bromide in water, acetonitrile, Time= 1h, T= 20 °C , Inert atmosphere Das, Rima; Chakraborty, Debashis; Applied Organometallic Chemistry; vol. 25; nb. 6; (2011); p. 437 - 442 View in Reaxys

87 %

With polysterene-bound phenylseleninic acid, dihydrogen peroxide in tetrahydrofuran, Time= 6h, Heating Qian, Hao; Shao, Li-Xiong; Huang, Xian; Journal of Chemical Research - Part S; nb. 10; (2002); p. 514 - 515 View in Reaxys

87 %

With tert.-butylhydroperoxide, Ammonium iron sulfate in water, dimethyl sulfoxide, Time= 7h, T= 80 °C , chemoselective reaction Chakraborty, Debashis; Majumder, Chandrima; Malik, Payal; Applied Organometallic Chemistry; vol. 25; nb. 7; (2011); p. 487 - 490 View in Reaxys

85 %

With tert.-butylhydroperoxide, bismuth(III) oxide in water, ethyl acetate, Time= 8h, Reflux, Kinetics Malik, Payal; Chakraborty, Debashis; Tetrahedron Letters; vol. 51; nb. 27; (2010); p. 3521 - 3523 View in Reaxys

85 %

With tert.-butylhydroperoxide, ammonium cerium (IV) nitrate in water, acetonitrile, Time= 24h, T= 20 °C Gowda, Ravikumar R.; Chakraborty, Debashis; Chinese Journal of Chemistry; vol. 29; nb. 11; (2011); p. 2379 2384 View in Reaxys

84 %

With dihydrogen peroxide, silver nitrate in acetonitrile, Time= 1.8h, T= 50 °C , chemoselective reaction Chakraborty, Debashis; Gowda, Ravikumar R.; Malik, Payal; Tetrahedron Letters; vol. 50; nb. 47; (2009); p. 6553 - 6556 View in Reaxys

81 %

With oxygen, Time= 168h, T= 20 °C , p= 760.051Torr , Neat (no solvent) Dintzner, Matthew R.; Mondjinou, Yawo A.; Pileggi, Dominic J.; Tetrahedron Letters; vol. 51; nb. 5; (2010); p. 826 - 827

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View in Reaxys 80 %

Stage 1: With tert.-butylhydroperoxide, tin(II) oxide in acetonitrile, Time= 1.66667h, T= 60 °C Stage 2: With hydrogenchloride in water, pH= 2.0 Dehbashi, Mohsen; Aliahmad, Mousa; Shafiee, Mohammad Reza Mohammad; Ghashang, Majid; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 188; nb. 7; (2013); p. 864 - 872 View in Reaxys

77 %

With hydrogenchloride, 4-amino-2-chloroperbenzoic acid in dichloromethane, Time= 4.5h, T= 20 °C Hashemi, Mohammed M.; Ghazanfari, Dadkhoda; Ahmadibeni, Yousef; Karimi-Jaberi, Zahed; Ezabadi, Ali; Synthetic Communications; vol. 35; nb. 8; (2005); p. 1103 - 1107 View in Reaxys

76.5 %

With [2,2]bipyridinyl, sulfuric acid, cetylpyridinium chloride, copper dichloride in water, T= 30 °C , Micellar solution, Green chemistry, Kinetics, Catalytic behavior, Reagent/catalyst Mondal, Monohar Hossain; Malik, Susanta; De, Sourav; Bhattacharyya, Subhendu Sekhar; Saha, Bidyut; Research on Chemical Intermediates; vol. 43; nb. 3; (2017); p. 1651 - 1670 View in Reaxys

72 %

With Oxonereg;, EDTA, sodium hydrogencarbonate in water, acetone, Time= 3.5h, T= 22 °C , Oxidation Webb, Kevin S.; Ruszkay, Stephen J.; Tetrahedron; vol. 54; nb. 3-4; (1998); p. 401 - 410 View in Reaxys

72 %

Stage 1: With potassium permanganate in acetone, Reflux Stage 2: With hydrogenchloride in water Zheng, Min-Yan; Wei, Yong-Sheng; Fan, Guang; Huang, Yi; Asian Journal of Chemistry; vol. 24; nb. 1; (2012); p. 161 - 164 View in Reaxys

70 %

With [Ni(cdacacen)], dihydrogen peroxide in water, acetonitrile, Time= 5h, T= 60 °C Esfandiari, Hadi; Jameh-Bozorghi, Saeed; Esmaielzadeh, Sheida; Shafiee, Mohammad Reza Mohammad; Ghashang, Majid; Research on Chemical Intermediates; vol. 39; nb. 7; (2013); p. 3319 - 3325 View in Reaxys

56.82 %

With pyridine, moisture, 1,2-Dichloro-3-iodobenzene, Time= 24h, Ambient temperature Mohandas, T. P.; Mamman, Ajit, S.; Nair, P. Madhavan; Tetrahedron; vol. 39; nb. 7; (1983); p. 1187 - 1188 View in Reaxys

55 %

With potassium bromate in acetic acid, Time= 0.25h, Heating Samaddar, Haraprasad; Banerjee, Amalendu; Journal of the Indian Chemical Society; vol. 59; nb. 7; (1982); p. 905 - 906 View in Reaxys

43 %

With sodium bromate, sodium hydrogensulfite, benzyl alcohol, Time= 2h, Ambient temperature Takase, Kiyoshi; Masuda, Haruyoshi; Kai, Osamu; Nishiyama, Yutaka; Sakaguchi, Satoshi; Ishii, Yasutaka; Chemistry Letters; nb. 10; (1995); p. 871 - 872 View in Reaxys

42.62 %

With oxygen, modified styrene-divinylbenzene polymer in neat (no solvent), other catalyst, Product distribution Prokop, Zdenek; Setinek, Karel; Collection of Czechoslovak Chemical Communications; vol. 46; nb. 11; (1981); p. 2657 - 2662 View in Reaxys With ferrocene, oxygen in acetonitrile, T= 35 °C , various other solvents; effect of solvent properties, Rate constant Vcelak, Jaroslav; Collection of Czechoslovak Chemical Communications; vol. 46; nb. 1; (1981); p. 201 - 218 View in Reaxys

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With phosphate buffer, permanganate(VII) ion in water, T= 25 °C , var. pH, Rate constant Freeman, Fillmore; Lin, Doris K.; Moore, Gregory R.; Journal of Organic Chemistry; vol. 47; nb. 1; (1982); p. 56 59 View in Reaxys With oligomer obtained from t-CH3CH2CH=CHCH2CH3, Ambient temperature, other reagent: oligomers obtained from c-CH3CH2CH=CHCH2CH3, or t- or c-(CH3)2CHCH=CHCH(CH3)2 in var. solvents, 5 weeks, Product distribution Murray, Robert W.; Su, Jang-Szu; Journal of Organic Chemistry; vol. 48; nb. 6; (1983); p. 817 - 822 View in Reaxys With bromamine T in perchloric acid, Time= 10h, T= 24.9 °C , various temperature, Kinetics, Mechanism Banerji, Kalyan K.; Tetrahedron; vol. 43; nb. 24; (1987); p. 5949 - 5954 View in Reaxys With potassium cyanide, hexamethyltrimethylammonium bromide, 3-methyl-10-(n-butyl)isoalloxazine in ethanol, water, T= 30 °C , other reagents, Rate constant Shinkai, Seiji; Yamashita, Takaharu; Kusano, Yumiko; Ide, Toyoko; Manabe, Osamu; Journal of the American Chemical Society; vol. 102; nb. 7; (1980); p. 2335 - 2340 View in Reaxys With bramamine-T, ruthenium trichloride in perchloric acid, T= 35 °C , var. bromamine-T concentrations, var. temperatures, effect of ionic strength of medium and addition of chloride and p-toluenesulfonamide, Rate constant, Mechanism, Kinetics Singh; Journal of the Indian Chemical Society; vol. 68; nb. 9; (1991); p. 494 - 496 View in Reaxys With NADPH tetrasodium salt, oxygen, cyclohexanone oxygenase in methanol, T= 15 °C , glycine, NaOH, pH=9.0, Rate constant Branchaud, Bruce P.; Walsh, Christopher T.; Journal of the American Chemical Society; vol. 107; (1985); p. 2153 - 2161 View in Reaxys With potassium hexacyanoperferrate, osmium(VIII) oxide in water, T= 35 °C , ΔE, -ΔS, PZ(sec-1); without cat.; NaCO3-NaHCO3 buffer, Rate constant, Thermodynamic data Khetawat, G. K.; Menghani, G. D.; Journal of the Indian Chemical Society; vol. 64; (1987); p. 766 - 768 View in Reaxys With diperiodato cuprate(III) in water, T= 39.9 °C , Rate constant Padmaja, S.; Rao, K. Nageshwar; Sethuram, B.; Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry; vol. 32; nb. 8; (1993); p. 685 - 688 View in Reaxys With nickel(IV) periodate in water, T= 26.9 °C , further temperature, Ea, ΔH(excit.), ΔG(excit.), ΔS(excit.), Kinetics, Mechanism, Thermodynamic data Chandraiah, U.; Murthy, C. P.; Kandlikar, Sushama; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 28; nb. 3; (1989); p. 248 - 249 View in Reaxys With potassium permanganate, perchloric acid, sodium fluoride in water, T= 24.9 °C , Rate constant Jain, Anandi L.; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 3; (1983); p. 678 - 692 View in Reaxys With ditelluratoargentate(III) in potassium hydroxide, T= 25.9 °C , other temperature, ΔE(excit.), ΔG(excit.), ΔH(excit.), ΔS(excit.), Thermodynamic data, Kinetics Raviprasad, T.; Sethuram, B.; Navaneeth Rao, T.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 19; nb. 3; (1980); p. 261 - 263

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View in Reaxys With perchloric acid, mercury(II) diacetate, N-bromoacetamide in water, T= 24.9 °C , also in alkaline solution (NaOH), Rate constant, Mechanism Sharma, Vinita; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 11; (1985); p. 3551 - 3574 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, hypochlorite, sodium bromide in water, T= 1.5 °C , pH 10; with/without TEMPO, Rate constant De Nooy; De Nooy, Arjan E. J.; Besemer; Besemer, Arie C.; Van Bekkum; Van Bekkum, Herman; Tetrahedron; vol. 51; nb. 29; (1995); p. 8023 - 8032 View in Reaxys With pyH(+)CO3(-), toluene-4-sulfonic acid in dimethyl sulfoxide, T= 24.9 °C , var. temperatures; ΔH(excit.); ΔS(excit.); ΔG(excit.), Rate constant, Thermodynamic data Khanchandani, Ritu; Sharma, Pradeep K.; Banerji, Kalyan K.; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 35; nb. 7; (1996); p. 576 - 579 View in Reaxys With N-bromobenzamide, mercury(II) diacetate in methanol, acetic acid, T= 24.9 °C , Rate constant Vyas, Vijay K.; Kothari, Seema; Banerji, Kalyan K.; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 35; nb. 2; (1996); p. 112 - 115 View in Reaxys durch Einw. von Aerobacter indologenes in einem Glucose enthaltenden Gaerensatz Mickelson,Werkman; ; vol. 37; (1939); p. 623; Chem. Zentralbl.; vol. 110; nb. II; (1939); p. 2342 View in Reaxys With air, cobalt salt, T= 100 - 165 °C Patent; Eastman Kodak Co.; US2294984; (1939) View in Reaxys With Mn(oleate)2, air, T= 45 °C Patent; Polymerisable Prod.Ltd.; US2456549; (1947) View in Reaxys With air, Co(oleate)2, T= 45 °C Patent; Polymerisable Prod.Ltd.; US2456549; (1947) View in Reaxys With copper chromite, steam, T= 314 °C Goldschmidt; Askenasy; Grimm; Chemische Berichte; vol. 67; (1934); p. 208 View in Reaxys Patent; Goldschmidt; Askenasy; Grimm; DE565476; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 937 View in Reaxys With oxygen, katalytische Oxydation Rector; ; vol. 2; (1948); p. 694 View in Reaxys Bernhauer; View in Reaxys Lorenz; View in Reaxys bei der Einw. von Bact.ascendens unter Luftabschluss

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Neuberg; Windisch; Biochemische Zeitschrift; vol. 166; (1925); p. 471; Naturwissenschaften; vol. 13; p. 994; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 1667 View in Reaxys With air, calcium carbonate, bei der Einw. von Bact.xylinum Neuberg; Windisch; Biochemische Zeitschrift; vol. 166; (1925); p. 471; Naturwissenschaften; vol. 13; p. 994; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 1667 View in Reaxys bei der Einw. von Schweineleberbrei Parnas; Biochemische Zeitschrift; vol. 28; (1910); p. 290 View in Reaxys With alkaline KMNO4, platinum Fournier; Bulletin de la Societe Chimique de France; vol. <4>7; (1910); p. 25 View in Reaxys With oxygen, platinum Fournier; Bulletin de la Societe Chimique de France; vol. <4>7; (1910); p. 25 View in Reaxys With air, lead oleate, T= 45 °C Patent; Polymerisable Prod.Ltd.; US2456549; (1947) View in Reaxys 90 % Chromat.

With dihydrogen peroxide, benzeneseleninic acid in tetrahydrofuran, Time= 2.5h, Heating Choi, Joong-Kwon; Chang, Young-Kil; Hong, Sung Yeap; Tetrahedron Letters; vol. 29; nb. 16; (1988); p. 1967 1970 View in Reaxys With bromamine T in perchloric acid, Time= 10h, T= 24.9 °C Banerji, Kalyan K.; Tetrahedron; vol. 43; nb. 24; (1987); p. 5949 - 5954 View in Reaxys With rat hepatic microsomal aldehyde dehydrogenase, NAD in phosphate buffer, N,N-dimethyl-formamide, T= 37 °C , pH= 7.4, Dehydrogenation, Enzyme kinetics Martini, Robert; Murray, Michael; Chemical Research in Toxicology; vol. 9; nb. 1; (1996); p. 268 - 276 View in Reaxys With N,N,N-trimethylbenzenemethanaminium dichloroiodate, acetic acid, zinc(II) chloride, T= 24.85 °C , Oxidation, Kinetics, Thermodynamic data, Further Variations: Temperatures Goswami, Garima; Kothari, Seema; Banerji, Kalyan K.; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 11; (1999); p. 1270 - 1273 View in Reaxys With tetra-N-butylammonium tribromide, potassium bromide in water, acetic acid, T= 24.85 - 54.85 °C , Kinetics Baghmar, Manju; Sharma, Pradeep K.; International Journal of Chemical Kinetics; vol. 33; nb. 6; (2001); p. 390 395 View in Reaxys With pyridinium chlorochromate in dimethyl sulfoxide, T= 24.85 °C , Kinetics, Further Variations: Temperatures Saraswat; Sharma; Banerji; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 40; nb. 6; (2001); p. 583 - 587 View in Reaxys With toluene-4-sulfonic acid, BPCC in dimethyl sulfoxide, T= 14.85 °C , Kinetics, Further Variations: Temperatures

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Kumbhat; Sharma; Banerji; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 39; nb. 11; (2000); p. 1169 - 1173 View in Reaxys With sulfuric acid, quinolinium dichromate(VI), Time= 24h, T= 30 - 35 °C , Kinetics Chaubey, Girija S.; Das, Simi; Mahanti, Mahendra K.; Croatica Chemica Acta; vol. 76; nb. 4; (2003); p. 287 - 291 View in Reaxys With benzyltriethylammonium chlorochromate, toluene-4-sulfonic acid in dimethyl sulfoxide, T= 24.85 °C , Kinetics, Further Variations: Temperatures Chouhan, Kavita; Rao, P.T.S.R.K. Prasad; Sharma, Pradeep K.; Journal of the Indian Chemical Society; vol. 83; nb. 2; (2006); p. 191 - 194 View in Reaxys With perchloric acid, tert-butylhypochlorite, acetic acid in water, T= 29.84 °C , Activation energy, Kinetics, Further Variations: Temperatures Gowda, B. Thimme; Moodithaya; Journal of the Indian Chemical Society; vol. 77; nb. 4; (2000); p. 194 - 196 View in Reaxys With oxygen Patent; Union Carbide Chemicals and Plastics Technology Corp.; US6362367; (2002); (B1) English View in Reaxys With MCC in dimethyl sulfoxide, T= 44.84 °C , Kinetics, Mechanism, Temperature Soni, Neelam; Tiwari, Vandana; Kumbhani; Shastri; Sharma, Vinita; Journal of the Indian Chemical Society; vol. 85; nb. 8; (2008); p. 857 - 861 View in Reaxys With oxygen in dichloromethane, Time= 4h, T= 14.84 °C , p= 759.826Torr Tada, Mizuki; Muratsugu, Satoshi; Kinoshita, Mutsuo; Sasaki, Takehiko; Iwasawa, Yasuhiro; Journal of the American Chemical Society; vol. 132; nb. 2; (2010); p. 713 - 724 View in Reaxys With air, Time= 2h Chudasama, Vijay; Fitzmaurice, Richard J.; Ahern, Jenna M.; Caddick, Stephen; Chemical Communications; vol. 46; nb. 1; (2010); p. 133 - 135 View in Reaxys With H2TMP, oxygen in dichloromethane, acetonitrile, Time= 48h, T= 20 °C , Irradiation Hajimohammadi, Mahdi; Safari, Nasser; Mofakham, Hamid; Shaabani, Ahmad; Tetrahedron Letters; vol. 51; nb. 31; (2010); p. 4061 - 4065 View in Reaxys With oxygen, dimethyl cis-but-2-ene-1,4-dioate in 1,4-dioxane, T= 60 °C Chudasama, Vijay; Fitzmaurice, Richard J.; Caddick, Stephen; Nature Chemistry; vol. 2; nb. 7; (2010); p. 592 596 View in Reaxys With Pisum sativum aminoaldehyde dehydrogenase 1, nicotinamide adenine dinucleotide, T= 20 °C , pH= 9, aq. buffer, Enzymatic reaction Tylichova, Martina; Kopecny, David; Morera, Solange; Briozzo, Pierre; Lenobel, Rene; Snegaroff, Jacques; Sebela, Marek; Journal of Molecular Biology; vol. 396; nb. 4; (2010); p. 870 - 882 View in Reaxys With Deinococcus geothermalis DSM 11300 aldehyde dehydrogenase, NAD, T= 30 °C , pH= 9, aq. buffer, Enzymatic reaction, Kinetics, Reagent/catalyst

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Wulf; Perzborn; Sievers; Scholz; Bornscheuer; Journal of Molecular Catalysis B: Enzymatic; vol. 74; nb. 1-2; (2012); p. 144 - 150 View in Reaxys With air, Time= 2h, T= 21 °C Chudasama, Vijay; Akhbar, Ahmed R.; Bahou, Karim A.; Fitzmaurice, Richard J.; Caddick, Stephen; Organic and Biomolecular Chemistry; vol. 11; nb. 42; (2013); p. 7301 - 7317 View in Reaxys With TPSD, toluene-4-sulfonic acid in dimethyl sulfoxide, T= 24.84 °C , Darkness, Kinetics, Temperature Patel; Poonam; Jha; Baghmar; Kothari; Shastri; Sharma, Pradeep K.; Journal of the Indian Chemical Society; vol. 89; nb. 8; (2012); p. 1149 - 1154 View in Reaxys With oxygen in water, Time= 6h, T= 100 °C , p= 2250.23Torr Gandarias, Inaki; Miedziak, Peter J.; Nowicka, Ewa; Douthwaite, Mark; Morgan, David J.; Hutchings, Graham J.; Taylor, Stuart H.; ChemSusChem; vol. 8; nb. 3; (2015); p. 473 - 480 View in Reaxys 2.3 Procedure and Kinetics Measurements Solutions of the oxidant and reaction mixtures containing known quantities of the substrate (butanal = 75*10-4 mol*dm-3), promoter (picolinic acid = 150*10-4 mol*dm-3, 2,2'-bipyridine = 125*10-4 mol*dm-3, 1,10-phenanthroline = 75*10-4 mol*dm-3) under the kinetics conditions [butanal]T>>[Cr(VI)]T and [promoter]T>>[Cr(VI)]T. The reactions were followed under pseudo-first-order conditions, using an excess of butanal over Cr(VI). Reactant solutions were previously thermostated and transferred into 1 cm path length cell immediately after mixing. Experiments were performed using 0.5(moldm-3) H2SO4 at 30°C. With 2-pyridinecarboxylic acid, potassium dichromate, sulfuric acid in water, T= 30 °C , p= 760.051Torr , pH= 2, Kinetics, Mechanism, Reagent/catalyst Malik, Susanta; Ghosh, Aniruddha; Saha, Bidyut; Journal of Solution Chemistry; vol. 45; nb. 1; (2016); p. 109 125 View in Reaxys 8 %Spectr. With C59H45BFeN6O3, oxygen in benzene, Time= 0.333333h, T= 20 °C Bhattacharya, Shrabanti; Rahaman, Rubina; Chatterjee, Sayanti; Paine, Tapan K.; Chemistry - A European Journal; vol. 23; nb. 16; (2017); p. 3815 - 3818 View in Reaxys

HO OH O

Rx-ID: 845511 View in Reaxys 2/804 Yield 100 %

Conditions & References With ammonium cerium (IV) nitrate, sodium trimethylsilylpropionate-d4, C18H22N4O2Ru(2+)*2F6P(1-), water, Time= 0.5h, T= 20 °C Hirai, Yuichirou; Kojima, Takahiko; Mizutani, Yasuhisa; Shiota, Yoshihito; Yoshizawa, Kazunari; Fukuzumi, Shunichi; Angewandte Chemie - International Edition; vol. 47; nb. 31; (2008); p. 5772 - 5776 View in Reaxys

99.7 %

With oxygen in water, Time= 24h, T= 80 °C , p= 760.051Torr Wang, Tao; Shou, Heng; Kou, Yuan; Liu, Haichao; Green Chemistry; vol. 11; nb. 4; (2009); p. 562 - 568 View in Reaxys

98.8 %

With potassium hydroxide, T= 50 °C , electrolysis Burzyk, Jerzy; Zjawiony, Ireneusz; Budniok, Antoni; Journal fuer Praktische Chemie (Leipzig); vol. 329; nb. 1; (1987); p. 131 - 136 View in Reaxys

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93 %

With oxygen, potassium carbonate, Pd nanoparticles, polystyrene-poly(ethylene glycol) resin in water, Time= 40h, p= 760Torr , Heating Uozumi, Yasuhiro; Nakao, Ryu; Angewandte Chemie - International Edition; vol. 42; nb. 2; (2003); p. 194 - 197 View in Reaxys

93 %

With oxygen, potassium carbonate, amphiphilic resin-dispersion of palladium nanoparticles in water, Time= 40h, p= 760.051Torr , Heating Uozumi, Yasuhiro; Nakao, Ryu; Rhee, Hakjune; Journal of Organometallic Chemistry; vol. 692; nb. 1-3; (2007); p. 420 - 427 View in Reaxys

92 %

Time= 15h, T= 25 °C , electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 0.18M KOH/tbutanol-water (1:1) Kaulen, Johannes; Schaefer, Hans-J.; Tetrahedron; vol. 38; nb. 22; (1982); p. 3299 - 3308 View in Reaxys

92 %

Time= 15h, T= 25 °C , electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 0.18M KOH/tbutanol - water (1:1); variation of electrolyte, temperature and reaction time, Product distribution Kaulen, Johannes; Schaefer, Hans-J.; Tetrahedron; vol. 38; nb. 22; (1982); p. 3299 - 3308 View in Reaxys

90 %

With Mn-trimethyltriazacyclononane, dihydrogen peroxide, sodium L-ascorbate in water, acetonitrile, T= 0 °C , Oxidation Berkessel, Albrecht; Sklorz, Christoph A.; Tetrahedron Letters; vol. 40; nb. 45; (1999); p. 7965 - 7968 View in Reaxys

88 %

With tert.-butylhydroperoxide, copper(ll) bromide in water, dimethyl sulfoxide, Time= 4.5h, T= 20 °C , Inert atmosphere Das, Rima; Chakraborty, Debashis; Applied Organometallic Chemistry; vol. 25; nb. 6; (2011); p. 437 - 442 View in Reaxys

86 %

With tert.-butylhydroperoxide, ammonium cerium (IV) nitrate in water, acetonitrile, Time= 30h, T= 20 °C Gowda, Ravikumar R.; Chakraborty, Debashis; Chinese Journal of Chemistry; vol. 29; nb. 11; (2011); p. 2379 2384 View in Reaxys

84 %

Stage 1: With C20H28ClN2OPRu, water, sodium hydroxide, Time= 18h, Inert atmosphere, Reflux Stage 2:Acidic conditions Balaraman, Ekambaram; Khaskin, Eugene; Leitus, Gregory; Milstein, David; Nature Chemistry; vol. 5; nb. 2; (2013); p. 122 - 125 View in Reaxys

83 %

With tert.-butylhydroperoxide, bismuth(III) oxide in water, ethyl acetate, Time= 55h, Reflux, Kinetics, Concentration, chemoselective reaction Malik, Payal; Chakraborty, Debashis; Synthesis; nb. 21; (2010); p. 3736 - 3740; Art.No: Z17610SS View in Reaxys

78.8 %

General procedure: The oxidation of alcohols was performed in an autoclave reactor equipped with a magnetic stirrer, thermocouple, automatic temperature controller and a pressure gauge. After the addition of desired amount of reactant, catalyst, water and NaOH, the autoclave was sealed. The atmosphere over the mixture was replaced with O2 for three times. Then the reactor was heated to the desired temperature with stirring. Subsequently, the pressure of O2 was charged to 1.0 MPa and kept constant during the reaction through feeding O2. When the reaction was finished, the reactor was cooled down to the ambient temperature. The reaction mixture was diluted with acetone to dissolve the products. After the catalyst was separated, the filtrate was acidified to pH of 2.0 by hydrochloric acid. The oxidation products were analyzed by gas chromatography equipped with a flame ionization detector. The isolated yield of carboxyl acid was obtained with the following procedure. The solvent of the mixture after acidification was removed through rotary evaporation. The pH of the residual was adjusted to 10.0 with NaOH (2.0 M), and then it

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was extracted with ethyl acetate for three times. The aqueous layer was acidified to pH 2.0 using HCl (6.0 M) and extracted with ethyl acetate. The organic layer was removed ethyl acetate through rotary evaporation to get the carboxylic acid. The carboxylic acid was dried overnight for calculation of the isolated yield. With Au NCs/TiO2, oxygen, sodium hydroxide in water, Time= 6h, T= 120 °C , p= 7500.75Torr , Autoclave, Green chemistry Zhou, Lipeng; Chen, Minzhu; Wang, Youqiang; Su, Yunlai; Yang, Xiaomei; Chen, Chen; Xu, Jie; Applied Catalysis A: General; vol. 475; (2014); p. 347 - 354 View in Reaxys 73 %

With hydrogenchloride, [Ru(CO)H2(MeN((CH2)2P(tBu2))2)], water, sodium hydroxide, Time= 20h, T= 120 °C , Inert atmosphere, Reflux, Catalytic behavior, Reagent/catalyst Choi, Jong-Hoo; Heim, Leo E.; Ahrens, Mike; Prechtl, Martin H. G.; Dalton Transactions; vol. 43; nb. 46; (2014); p. 17248 - 17254 View in Reaxys

62.4 %

5B : (Synthesis of n- butane acid from n- butyl alcohol) Example 5B Eggplant flask 50 ml, Example 2 and the residue obtained by the same method (Ru-Ir-Re / AC catalyst (2)), n- butyl alcohol 0.741mg of (10.0 mmol)was added, n- butyl alcohol has been filled up with water so as to be 10percent. This was heated to reflux with stirring for 54 hours.After completion of the reaction, the resulting reaction solution was cooled to room temperature and then filtered through a syringe equipped with amembrane filter (0.45 μm).The obtained filtrate was analyzed by gas chromatography, n- conversion of butyl alcohol is 97.6percent n-yield butanoic acid 47.0percent the selectivity was48.2percent there were. The catalyst used in the examples. 2A, obtained Rh-PtRe / SiO Example 5 2 changed to the catalyst (1) 288 mg, reaction 180 ° C. in except forchanging the 24 hours, the reaction was conducted in the same manner as in example. 2A, and 28.7percent for the conversion of n- propyl alcohol, theyield of propionic acid 14.9percent, the selection the rate was 51.9percent in Example 5A, n- propyl alcohol changed to a n- butyl alcohol 0.741mg (10.0mmol), 6-hour reaction at 180 , Furthermore, except for changing to200 in 30 hours, where the reaction was carried out in the same manner as in example 5A, 82.4 percent conversion rate of n- butyl alcohol, theyield of n- butane acid 62. 4percent, the selectivity was 75.4percent. With water, Time= 36h, T= 180 - 200 °C , p= 7500.75Torr , Autoclave, Inert atmosphere, Reagent/catalyst, Temperature Patent; UBE INDUSTRIES LIMITED; YOSHII, KIYOTAKA; YAMADA, ATSUSHI; WADA, NOBUHIRO; (25 pag.); JP2015/203010; (2015); (A) Japanese View in Reaxys

60 %

With superoxide, oxygen in N,N-dimethyl-formamide, Time= 15h, electrolysis, divided electrolytic cell, mercury pool cathode, platinum foil anode, Bu4N+Br-, cyclohexene, constant potential -1.0 V vs. SCE, current 112 (initial) to 15 (final) mA Singh; Dwivedi; Misra; Synthesis; nb. 4; (1991); p. 291 - 293 View in Reaxys

43 %

With O40PW12 (3-)*C30H60N3 (3+), dihydrogen peroxide in water, Time= 6h, T= 90 °C He, Ying; Ma, Xiaoyun; Lu, Ming; Arkivoc; vol. 2012; nb. 8; (2012); p. 187 - 197 View in Reaxys With nitric acid Patent; Celanese Corp.Am.; GB771583; (1955) View in Reaxys bei der Vergaerung durch Methanobacterium omelianskii Barker; ; vol. 7; (1936); p. 411; Chem. Zentralbl.; vol. 108; nb. I; (1937); p. 1707 View in Reaxys Barker; Journal of Biological Chemistry; vol. 137; (1941); p. 157 View in Reaxys With cerium (IV) sulfate, sulfuric acid, elektrolytische Oxydation an Bleianoden

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Radtschenko; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 10; (1937); p. 683; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 13; (1940); p. 1348; ; (1941); p. 2469; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 294 View in Reaxys With manganese(II) sulfate, sulfuric acid, elektrolytische Oxydation an Bleianoden Jerschow; Pjatnitzkaja; ; nb. 1; (1940); p. 29; ; (1940); p. 4673 View in Reaxys With sodium hydroxide, T= 300 °C , unter Druck Patent; Dow Chem.Co.; US1934648; (1932) View in Reaxys Patent; du Pont de Nemours and Co.; US1856263; (1929) View in Reaxys With potassium hydroxide, sodium hydroxide, T= 300 °C , unter Druck Patent; Dow Chem.Co.; US1934648; (1932) View in Reaxys Patent; du Pont de Nemours and Co.; US1856263; (1929) View in Reaxys With sodium hydroxide, cadmium(II) oxide, T= 235 - 250 °C , unter Druck Patent; Carbide and Carbon Chem.Corp.; US2384817; (1942) View in Reaxys With potassium hydroxide, sodium hydroxide, cadmium(II) oxide, T= 235 - 250 °C , unter Druck Patent; Carbide and Carbon Chem.Corp.; US2384817; (1942) View in Reaxys With oxygen, katalytische Oxydation Rector; ; vol. 2; (1948); p. 694 View in Reaxys Bernhauer; View in Reaxys Lorenz; View in Reaxys With calcium, T= 235 °C Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys With calcium oxide, T= 250 °C Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys With alkaline permanganate solution Fournier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 144; (1907); p. 333; Bulletin de la Societe Chimique de France; vol. <4>5; (1909); p. 920 View in Reaxys With cobalt(II) acetate, acetaldehyde, acetic acid, T= 120 - 130 °C , mit Luft Patent; Eastman Kodak Co.; US2552175; (1948) View in Reaxys 83 % Turn- Irradiation, W lamp ov. Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 2; (1982); p. 245 - 255

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View in Reaxys With oxygen, sodium carbonate, platinum on activated charcoal in water, T= 50 °C , p= 750.06Torr , Mechanism, Rate constant Nondek, Lubomir; Zdarova, Dana; Malek, Jaroslav; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 47; nb. 4; (1982); p. 1121 - 1129 View in Reaxys With sodium hydroxide, potassium hexacyanoferrate(III), iridium(III) chloride, T= 35 °C , ΔE, ΔS(excit.), ΔF(excit.), Rate constant, Thermodynamic data Singh; Tandon; Mehrotra; Journal of the Indian Chemical Society; vol. 67; nb. 6; (1990); p. 458 - 462 View in Reaxys With perchloric acid, potassium chloride, bromamine T, ruthenium trichloride, effect of concentration of reactants and chloride ion, pH and temperature was investigated, Kinetics, Rate constant Singh, Bharat; Singh, A. K.; Singh, N. B.; Saxena, B. B. L.; Tetrahedron; vol. 40; nb. 24; (1984); p. 5203 - 5206 View in Reaxys With dipotassium peroxodisulfate in water, mechanism, concentration, temperature, overall energy of activation, Kinetics, Rate constant, Thermodynamic data Beylerian, N. M.; Khachatrian, A. G.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1984); p. 1937 - 1942 View in Reaxys With sodium hydroxide, potassium permanganate, T= 25 °C , I = 2.0 mol dm3; var. conc. of MeOH and NaOH, var. ionic strength, also axidation by manganate, Rate constant Szammer, J; Jaky, M; Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry; vol. 31; nb. 7; (1992); p. 417 - 422 View in Reaxys With immobilized cells of Clostridium acetobutylicum ATCC 824, T= 37 °C , pH 5.5-7.0; effect of pH on product formation investigated, Product distribution Taya, Masahito; Yagi, Toshiyuki; Kobayashi, Takeshi; Agricultural and Biological Chemistry; vol. 50; nb. 8; (1986); p. 2141 - 2142 View in Reaxys With sodium hydroxide, potassium hexacyanoferrate(III), ruthenium tetroxide, T= 35 °C , Mechanism, Rate constant Singh, M. P.; Singh, R. M.; Tandon, P. K.; Mehrotra, Alka; Thakur, P.; Journal of the Indian Chemical Society; vol. 65; nb. 10; (1988); p. 720 - 723 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, hypochlorite, sodium bromide in water, T= 1.5 °C , pH 10; with/without TEMPO, Rate constant De Nooy; De Nooy, Arjan E. J.; Besemer; Besemer, Arie C.; Van Bekkum; Van Bekkum, Herman; Tetrahedron; vol. 51; nb. 29; (1995); p. 8023 - 8032 View in Reaxys 99.7 % Chromat.

With oxygen, Pt-GLY in water, Time= 24h, T= 80 °C , p= 760.051Torr Wang, Tao; Xiao, Chao-Xian; Yan, Liang; Xu, Lin; Luo, Jie; Shou, Heng; Kou, Yuan; Liu, Haichao; Chemical Communications; nb. 42; (2007); p. 4375 - 4377 View in Reaxys With sodium hydroxide, oxygen, Au/C, Time= 2h, T= 70 °C , p= 2280.15Torr , Product distribution, Further Variations: Catalysts Biffis, Andrea; Cunial, Sara; Spontoni, Paolo; Prati, Laura; Journal of Catalysis; vol. 251; nb. 1; (2007); p. 1 - 6 View in Reaxys

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Stage 1: With gold on titanium oxide in water, Time= 0.166667h, T= 90 °C , Inert atmosphere Stage 2: With dihydrogen peroxide in water, Time= 1.08333h, T= 90 °C , Inert atmosphere, chemoselective reaction Ni, Ji; Yu, Wen-Jian; He, Lin; Sun, Hao; Cao, Yong; He, He-Yong; Fan, Kang-Nian; Green Chemistry; vol. 11; nb. 6; (2009); p. 756 - 759 View in Reaxys With methyltrifluoromethyldioxirane in dichloromethane, Time= 8h, T= -15 °C , Darkness Mello, Rossella; Martinez-Ferrer, Jaime; Alcalde-Aragones, Ana; Varea, Teresa; Acerete, Rafael; GonzalezNunez, Maria Elena; Asensio, Gregorio; Journal of Organic Chemistry; vol. 76; nb. 24; (2011); p. 10129 - 10139 View in Reaxys 87 %Chromat.

With dihydrogen peroxide, copper dichloride, Time= 4.16667h, T= 25 °C , Ionic liquid Karthikeyan, Parasuraman; Aswar, Sachin Arunrao; Muskawar, Prashant Narayan; Bhagat, Pundlik Rambhau; Kumar, S. Senthil; Catalysis Communications; vol. 26; (2012); p. 189 - 193 View in Reaxys

94 %Spectr.

With sodium periodate, C18H25ClIrNO in water-d2, Time= 1h, T= 23 °C , Inert atmosphere Zhou, Meng; Hintermair, Ulrich; Hashiguchi, Brian G.; Parent, Alexander R.; Hashmi, Sara M.; Elimelech, Menachem; Periana, Roy A.; Brudvig, Gary W.; Crabtree, Robert H.; Organometallics; vol. 32; nb. 4; (2013); p. 957 - 965 View in Reaxys With oxygen in toluene, Time= 24h, T= 100 °C , p= 7500.75Torr , Temperature Wang, Min; Wang, Feng; Ma, Jiping; Chen, Chen; Shi, Song; Xu, Jie; Chemical Communications; vol. 49; nb. 59; (2013); p. 6623 - 6625 View in Reaxys With Pt#Bi2O3, oxygen in water, Time= 5h, T= 90 °C , p= 750.075Torr , Autoclave, Reagent/catalyst Lu, Tianliang; Du, Zhongtian; Liu, Junxia; Ma, Hong; Xu, Jie; Green Chemistry; vol. 15; nb. 8; (2013); p. 2215 2221 View in Reaxys

0.56 mol

With tert.-butylhydroperoxide, tetra-tert-butoxychromium in benzene, T= 20 °C Stepovik; Potkina; Poddelskii; Russian Journal of General Chemistry; vol. 83; nb. 11; (2013); p. 2005 - 2017; Zh. Obshch. Khim.; vol. 83; nb. 11; (2013); p. 1805 - 1818,14 View in Reaxys With 2O39PW11 (7-)*11K(1+)*Pr(3+)*22H2O, dihydrogen peroxide in water, Time= 8h, T= 90 °C , Green chemistry Saini, Mukesh Kumar; Gupta, Rakesh; Parbhakar, Swati; Singh, Surendra; Hussain, Firasat; RSC Advances; vol. 4; nb. 72; (2014); p. 38446 - 38449 View in Reaxys With oxygen in water, Time= 6h, T= 100 °C , p= 2250.23Torr Gandarias, Inaki; Miedziak, Peter J.; Nowicka, Ewa; Douthwaite, Mark; Morgan, David J.; Hutchings, Graham J.; Taylor, Stuart H.; ChemSusChem; vol. 8; nb. 3; (2015); p. 473 - 480 View in Reaxys

98 %Spectr.

With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy, sodium hydrogencarbonate, sodium carbonate in aq. buffer, Time= 2h, pH= 10, Electrochemical reaction, Catalytic behavior, Reagent/catalyst Rafiee, Mohammad; Miles, Kelsey C.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 137; nb. 46; (2015); p. 14751 - 14757 View in Reaxys

70 %Spectr.

7 :A stock solution of KHSO5 was prepared in degassed D20 under N2. Catalyst (e.g., Co-dppe) was added to each reaction tube. The tubes were then evacuated under vacuum and refilled with N2 several times. 400 jtL of d5-acetone was added to each tube followed by the appropriate substrate. Reactions were initiated by the addition of 100

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pL of KHSO5 stock solution. Reactions were monitored for 3 or 15 hrs depending on the substrate. The reactions were quenched by addition of a stock solution of d4-sodium trimethylsilyl propionate (NMR internal standard) and d5dim- ethylsulfoxide (oxidant quench). The reactions stirred another 15 mm and then were filtered into NMR tubes. The reactions were quantified by NMR. (Control reactions were performed without catalyst and in each case the substrate conversion is >5percent)10209] For most of the substrates selective oxidation to a single product was observed. The catalyst system was able to oxidize unactivated alkanes to a single product but in low yield. Oxidation of 1 -butanol illustrates the difference the catalyst and simple cobalt salts. The catalyst selectively oxidizes butanol to butyric acid whereas the CoOl) salts tested were highly unselective, affording several different products. With oxone in [(2)H6]acetone, Time= 3h, Inert atmosphere Patent; Yale University; Bloomfield, Aaron J.; Sheehan, Stafford W.; Collom, Samuel L.; Crabtree, Robert H.; Anastas, Paul T.; (31 pag.); US2016/152648; (2016); (A1) English View in Reaxys 95 %Chromat.

Oxidation of primary alkanols 1a—h with H2O2—HBr in methanol or in a water—methanol mixture (general procedure). General procedure: To a vigorously stirred solution of alkanol 1 (1 mmol) in 48percent HBr in MeOH or MeOH—H2O, a solution of H2O2 (35percent) in the corresponding solvent (1—1.5 mL) was added by portions (0.2—0.25 mL) at 65—70 °C (the reagent molar ratios are given in Tables 3 and 4). After addition of the first portion of the H2O2 solution, the reaction mixture turned to light yellow and after 20—30 min was colorless. Then the next portion of hydrogen peroxide was added. After completion of the reaction, the mixture was cooled, extracted with diethyl ether (3×15 mL), the combined organic layers were washed with water, dried with MgSO4, and the solvent was removed in vacuo. The conversions of alkanols and the product yields were determined by GC. With water, hydrogen bromide, dihydrogen peroxide in methanol, T= 65 - 70 °C Nikishin; Sokova; Terent´ev; Kapustina; Russian Chemical Bulletin; vol. 64; nb. 12; (2015); p. 2845 - 2850; Izv. Akad. Nauk, Ser. Khim.; nb. 12; (2015); p. 2845 - 2850,6 View in Reaxys 38 :lower alcohols (ethanol, 1-propanol, 1-butanol) and mixtures of water with the raw material and obtaining hydrogen At the same time, the catalytic reaction to obtain carboxylic acid with corresponding number of carbons was studied.First, an anionic catalyst 3 (3.0 molpercent) and sodium hydroxide (3.0 molpercent) were added to a mixture of ethanol (10 mmol) and water (20 mmol) and reacted under reflux conditions for 20 hours to give acetic acid Was produced at a yield of 85percent, and 445 mL (yield: 92percent) of hydrogen was obtained (entry 1).In addition, when a similar reaction using a mixture of 1-propanol and water was carried out over 40 hours, propionic acid was obtained in a yield of 68percent and 411 mL of hydrogen (yield: 85percent) occurred.In this reaction, a small amount (18percent) of an ester product (propyl propionate) was also observed (entry 2).Furthermore, the same carboxylic acid formation reaction progressed by reaction using a mixture of 1-butanol and water as a raw material, and butyric acid could be obtained with generation of hydrogen (entry 3 and 4). With C20H22IrN2O3 (1-)*Na(1+), sodium hydroxide in water, Time= 40h, Time Patent; KANTO CHEM CO INC; YAMAGUCHI, RYOHEI; FUJITA, KENICHI; (38 pag.); JP2015/83544; (2015); (A) Japanese View in Reaxys

80.5 3 : Example 3 %Chromat. A method for preparing a low-carbon fatty acid,The specific operation is as follows:Weigh 185g 1-butanol,75 g of water and 75 g of urea were stirred at room temperature,2550 g of 10percent hydrogen peroxide was added dropwise,Maintain 35 reaction 18h,Gas chromatography analysis,Unreacted raw materials butanol 14.8percentProduct 80.5percent, by liquid, distillation, butyric acid finished. With dihydrogen peroxide, urea in water, Time= 18h, T= 35 °C Patent; Huangshan Kehong Bio-flavors Co., Ltd.; Cheng, Cunzhao; Gu, Weimin; Wang, Zhijian; (4 pag.); CN106336354; (2017); (A) Chinese View in Reaxys

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HO O

NH 2

Rx-ID: 1763407 View in Reaxys 3/804 Yield

Conditions & References With sulfuric acid, water, uranyl acetate, T= 10 °C , Irradiation, quenching constants, Quantum yield, Mechanism Brar, A. S.; Chander, R.; Kohli, K. B.; Sandhu, S. S.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 21; nb. 3; (1982); p. 231 - 235 View in Reaxys With hydrogenchloride in water, T= 60 °C , various concentrations, Mechanism, Kinetics Mittal, S.; Gupta, K. S.; Gupta, Y. K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 21; nb. 4; (1982); p. 357 - 360 View in Reaxys With Rhodococcus erythropolis TA37 acylamidase, Time= 0.333333h, T= 37 °C , pH= 7.5, aq. buffer, Enzymatic reaction, Kinetics Lavrov; Zalunin; Kotlova; Yanenko; Biochemistry (Moscow); vol. 75; nb. 8; (2010); p. 1006 - 1013 View in Reaxys With Flavobacterium aquatile strain ZJB-09211 in water, T= 30 °C , Microbiological reaction Xu, Jian-Miao; Chen, Ben; Wang, Yuan-Shan; Zheng, Yu-Guo; Chemical Papers; vol. 67; nb. 10; (2013); p. 1262 - 1270 View in Reaxys 2.9 Substrate specificity and stereoselectivity General procedure: The substrate specificity of recombinant KamH was tested using various aliphatic and aromatic amides. Cell-free extract of E. coli BL21(DE3)/pET-Ami2 was mixed with various concentrations of substrate under standard reaction conditions; 10percent (v/v) methanol was added as cosolvent to solubilize the substrate. The enzyme activity toward the various amides was determined by monitoring the formation of either carboxylic acid or ammonia [36]. Several racemic amides were used to study the stereoselectivity of the recombinant enzyme, including 2phenylacetamide, mandelamide, 2,2-dimethylcyclopropanecarboxamide, and 2-(4-chlorophenyl)-3-methylbutyramide. Enantiomeric excess values were obtained by HPLC analysis using an AY-RH column. The enantiomeric excess and enantiomeric ratio of the product were determined according to Chen et al. [37]. With cell-free extract of amidase gene cloned from Klebsiella oxytoca KCTC 1686 and functionally expressed in Escherichia coli BL21(DE3) in methanol, Enzymatic reaction Guo, Fa-Mou; Wu, Jian-Ping; Yang, Li-Rong; Xu, Gang; Process Biochemistry; vol. 50; nb. 8; (2015); p. 1264 1271 View in Reaxys With water in aq. phosphate buffer, Time= 0.5h, T= 37 °C , pH= 7, Enzymatic reaction Ismailsab, Mukram; Monisha; Reddy, Pooja V.; Santoshkumar; Nayak, Anand S.; Karegoudar, Timmanagouda B.; Biocatalysis and Biotransformation; vol. 35; nb. 1; (2017); p. 74 - 85 View in Reaxys

O N

O O

O N

Rx-ID: 1995207 View in Reaxys 4/804 Yield

Conditions & References With alkaline solution in water, acetonitrile, T= 24.9 - 25.1 °C , carbonate buffer pH 10.70, Rate constant Matta, Michael S.; Broadway, Dale E.; Stroot, Michele K.; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 4916 - 4918 View in Reaxys With 1-methyl-1H-imidazole, 2-(cyclohexylamino)ethanesulfonic acid in acetonitrile, T= 27 °C , Rate constant

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Gagliano, Ronald A.; Knowlton, Robert C.; Byers, Larry D.; Journal of Organic Chemistry; vol. 54; nb. 22; (1989); p. 5247 - 5250 View in Reaxys With Carbonate buffer, alpha cyclodextrin in water, dimethyl sulfoxide, T= 25 °C , also with β-cyclodextrin, Rate constant Tee, Oswald S.; Mazza, Charles; Lozano-Hemmer, Rafael; Giorgi, Javier B.; Journal of Organic Chemistry; vol. 59; nb. 25; (1994); p. 7602 - 7608 View in Reaxys With phosphate buffer pH 11.6, dimethyl-β-cyclodextrin in water, T= 25 °C , reaction with γ-cyclodextrin or without cyclodextrin reagent, Rate constant Tee, Oswald S.; Gadosy, Timothy A.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 10; (1994); p. 2191 - 2198 View in Reaxys With captisol®, T= 25 °C , in a phosphate buffer (pH 11.6); effect of simple alcohols on cleavage rate, Rate constant Tee, Oswald S.; Bozzi, Massimo; Clement, Nicolas; Gadosy, Timothy A.; Journal of Organic Chemistry; vol. 60; nb. 11; (1995); p. 3509 - 3517 View in Reaxys With bovine pancreatic cholesterol esterase, phenyl-N-butylcarbamate, water, different substituted phenyl-N-butylcarbamates, Rate constant Lin, Gialih; Lai, Cheng-Yue; Tetrahedron Letters; vol. 36; nb. 34; (1995); p. 6117 - 6120 View in Reaxys With octa(dimethylaminopropyl)resorcinlt;4gt;arene, water, T= 25 °C , Rate constant Pirrincioglu, Necmettin; Zaman, Flora; Williams, Andrew; Journal of the Chemical Society. Perkin Transactions 2; vol. 1996; nb. 12; (1996); p. 2561 - 2562 View in Reaxys With pH 11.6 phosphate buffer, cetyltrimethylammonim bromide, sodium bromide in acetonitrile, T= 25 °C , Rate constant Tee; Fedortchenko; Canadian Journal of Chemistry; vol. 75; nb. 10; (1997); p. 1434 - 1438 View in Reaxys With pH=5.1 buffer, polypeptide KO-42 in water, acetonitrile, T= 16.9 °C , other polypetides vith var. amino acids sequences, Rate constant Broo, Kerstin S.; Nilsson, Helena; Nilsson, Jonas; Baltzer, Lars; Journal of the American Chemical Society; vol. 120; nb. 40; (1998); p. 10287 - 10295 View in Reaxys With MES buffer, water, 1-Dodecyl-4-[1-(hydroxyimino)ethyl]pyridinium bromide, T= 25 °C , pH= 7.2, Hydrolysis, Kinetics, Further Variations: Reagents Cibulka, Radek; Hampl, Frantisek; Kotoucova, Hana; Mazac, Jiri; Liska, Frantisek; Collection of Czechoslovak Chemical Communications; vol. 65; nb. 2; (2000); p. 227 - 242 View in Reaxys With human serum albumin in phosphate buffer, T= 25 °C , pH= 7.4, Activation energy, Further Variations: Temperatures Sakurai, Yuji; Ma, Shen-Feng; Watanabe, Hiroshi; Yamaotsu, Noriyuki; Hirono, Shuichi; Kurono, Yukihisa; Kragh-Hansen, Ulrich; Otagiri, Masaki; Pharmaceutical Research; vol. 21; nb. 2; (2004); p. 285 - 292 View in Reaxys With sodium phosphate buffer, Aspergillus niger ZD11 pyrethroid hydrolase in acetonitrile, T= 30 °C , pH= 6.8, Enzyme kinetics

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Liang, Wei Q.; Wang, Zhuo Y.; Li, He; Wu, Pei C.; Hu, Ji M.; Luo, Na; Cao, Li X.; Liu, Yu H.; Journal of Agricultural and Food Chemistry; vol. 53; nb. 19; (2005); p. 7415 - 7420 View in Reaxys With sodium phosphate buffer, Klebsiella sp. ZD112 pyrethroid-hydrolyzing esterase in acetonitrile, T= 30 °C , pH= 7.0, Enzyme kinetics Wu, Pei C.; Liu, Yu H.; Wang, Zhuo Y.; Zhang, Xiao Y.; Li, He; Liang, Wei Q.; Luo, Na; Hu, Ji M.; Lu, Jia Q.; Luan, Tian G.; Cao, Li X.; Journal of Agricultural and Food Chemistry; vol. 54; nb. 3; (2006); p. 836 - 842 View in Reaxys With hexa-arginine tagged esterase, Enzyme kinetics, Further Variations: Reagents Ha, Tai Hwan; Jeong, Jin Young; Chung, Bong Hyun; Chemical Communications; nb. 31; (2005); p. 3959 - 3961 View in Reaxys With Burkholderia xenovorans LB400 BphD in phosphate buffer, T= 25 °C , pH= 7.0, Enzyme kinetics Li, Jian-Jun; Bugg, Timothy D. H.; Organic and Biomolecular Chemistry; vol. 5; nb. 3; (2007); p. 507 - 513 View in Reaxys With phosphate buffer, subtilisin in water, T= 37 °C , pH= 5, Enzyme kinetics, Further Variations: Reagents, pH-values Nakashima, Kazunori; Maruyama, Tatsuo; Kamiya, Noriho; Goto, Masahiro; Organic and Biomolecular Chemistry; vol. 4; nb. 18; (2006); p. 3462 - 3467 View in Reaxys With 6-aminohexanoate cyclic dimer hydrolase Arthrobacter sp., T= 30 °C , pH= 7, aq. phosphate buffer, Enzymatic reaction Yasuhira, Kengo; Shibata, Naoki; Mongami, Go; Uedo, Yuki; Atsumi, Yu; Kawashima, Yasuyuki; Hibino, Atsushi; Tanaka, Yusuke; Lee, Young-Ho; Kato, Dai-Ichiro; Takeo, Masahiro; Higuchi, Yoshiki; Negoro, Seiji; Journal of Biological Chemistry; vol. 285; nb. 2; (2010); p. 1239 - 1248 View in Reaxys With Acinetobacter johnsonii dioxygenase Dke1, T= 25 °C , pH= 7.5, aq. buffer, Enzymatic reaction, Kinetics, Reagent/catalyst, Time Leitgeb, Stefan; Nidetzky, Bernd; ChemBioChem; vol. 11; nb. 4; (2010); p. 502 - 505 View in Reaxys With water, T= 20 °C , pH= 8 Laveille; Phuoc, L. Truong; Drone; Fajula; Renard; Galarneau; Catalysis Today; vol. 157; nb. 1-4; (2010); p. 94 100 View in Reaxys With human intestinal carboxylesterase, pH= 7.4, aq. buffer, Enzymatic reaction, Kinetics, Reagent/catalyst Hatfield; Tsurkan; Hyatt; Yu; Edwards; Hicks; Wadkins; Potter; British Journal of Pharmacology; vol. 160; nb. 8; (2010); p. 1916 - 1928 View in Reaxys With EstEH112 esterase, water, T= 25 °C , pH= 8, GTA buffer, Enzymatic reaction, Kinetics, pH-value, Temperature, Solvent, Reagent/catalyst Oh, Ki-Hoon; Nguyen, Giang-Son; Kim, Eun-Young; Kourist, Robert; Bornscheuer, Uwe; Oh, Tae-Kwang; Yoon, Jung-Hoon; Journal of Molecular Catalysis B: Enzymatic; vol. 80; (2012); p. 67 - 73 View in Reaxys 2.5. Enzyme assay General procedure: The standard esterase assay was carried out with an artificial chromogenic substrate, p-nitrophenyl (PNP) caprate (C10), with a modified version of the Stöcklein method using emulsifiers [15,18]. The enzyme reaction was started by the addition of 0.1 ml of freshly prepared and prewarmed PNP-caprate solution (5 mM), as the substrate, to 0.1 ml of the purified esterase enzyme solution (15 μg/ml) and 0.8 ml of prewarmed 100 mM Tris–

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HCl buffer (pH 8.0) containing sodium taurocholate (2 mg/ml) and gum arabic (1 mg/ml), as emulsifiers, in cells held in the cell holder at 60 °C or at a desired temperature. The initial velocity of the reaction was measured by monitoring changes in absorbance at 405 nm using a spectrophotometer (Shimatzu UV2401PC) fitted with a temperature controlled cell holder. One unit of esterase was defined as the amount of the enzyme releasing 1μmol of p-nitrophenol per min. The extinction coefficients of p-nitrophenol were determined prior to the measurements under each condition. In every measurement, the effect of nonenzymatic hydrolysis of substrates was taken into consideration and subtracted from the value measured when the enzyme was added. Measurements were carried out at least three times. Standard deviations never exceeded 10percent of the mean values. For the determination of substrate specificity, other kinds of p-nitrophenyl (PNP) esters such as PNP-butyrate (C4, 0.02–5 mM), PNP-caproate (C6, 0.01–1 mM), PNP-caprylate (C8, 0.01–1 mM), PNP-caprate (C10, 0.01–1 mM), PNP-laurate (C12, 0.02–2 mM), and PNP-palmitate (C16, 0.02–5 mM) were also used as substrates. Activities for all substrates were determined as described above. With hydrogenchloride, recombinant Sulfolobus solfataricus P1 esterase, water, sodium taurocholate, 2-amino-2-hydroxymethyl-1,3-propanediol, T= 60 °C , pH= 8.0, Enzymatic reaction, Kinetics Nam, Jae-Kyung; Park, Young-Jun; Lee, Hee-Bong; Journal of Molecular Catalysis B: Enzymatic; vol. 94; (2013); p. 95 - 103 View in Reaxys With carboxylesterase EstSt7 from Sulfolobus tokodaii strain 7, water in ethanol, T= 80 °C , pH= 9, Enzymatic reaction, Kinetics, Temperature, pH-value Wei, Tao; Feng, Shengxue; Shen, Yulong; He, Peixin; Ma, Geli; Yu, Xuan; Zhang, Fei; Mao, Duobin; Journal of Molecular Catalysis B: Enzymatic; vol. 97; (2013); p. 225 - 232 View in Reaxys With lipase from Candida rugosa in aq. phosphate buffer, pH= 7, Enzymatic reaction, Catalytic behavior Hong, Sung-Gil; Kim, Han Sol; Kim, Jungbae; Langmuir; vol. 30; nb. 3; (2014); p. 911 - 915 View in Reaxys With lipase immobilized poly(ethylene glycol)-decorated polystyrene in isopropyl alcohol, T= 25 °C , Enzymatic reaction, Catalytic behavior, Reagent/catalyst Silva, Rubens A.; Carmona-Ribeiro, Ana M.; Petri, Denise F.S.; Molecules; vol. 19; nb. 6; (2014); p. 8610 - 8628 View in Reaxys 2.10. Substrate specificity and kinetics parameters General procedure: Esterase activity was determined according to the method of Sumby et al. [15] using pNPA as the substrate with minor modifications. A 50-μl aliquot of suitably diluted enzyme solution was added to 400 μl 2 mM pNPA substrate solution (prepared in 50 mM Tris–HCl buffer pH 7.5) containing 10percent (v/v) isopropanol, and incubated at 50 °C for 10 min. Then the reaction was stopped by adding 500 μl of 300 mM phosphate buffer (pH 7.0) containing 5percent (w/v) SDS. The liberated pNP was quantified by measuring the absorbance at 410 nm. One unit of enzyme activity was defined as the amountof enzyme required to liberate 1 μmol pNP per minute under the above assay conditions. Substrate specificity of RmEstB was examined by measuring the enzyme’s activity toward the pNP esters (pNPA, pNPB, pNPH, pNPC, pNPD, pNPL, pNPM and pNPP), and the synthetic triacylglycerol substrates (triacetin, tributyrin, tricaproin and tricaprylin). For the pNP ester substrates, the measurement was the same as for the enzyme assay, except that the substrate solution contained 0.1percent (v/v) TritonX-100 and 0.1percent (w/v) arabic gum in addition to the different pNP esters [36]. With recombinant esterase from Rhizomucor miehei in isopropyl alcohol, Time= 0.166667h, T= 50 °C , pH= 7.5, Enzymatic reaction, Catalytic behavior, Kinetics Yan, Qiao-Juan; Yang, Shao-Qing; Duan, Xiao-Jie; Xu, Hai-Bo; Liu, Yu; Jiang, Zheng-Qiang; Journal of Molecular Catalysis B: Enzymatic; vol. 109; (2014); p. 76 - 84 View in Reaxys 2.3. Lipase inhibition assay The blue spot on the TLC plate was scrapped and suspended in the water sufficient to submerge the silica gel for 3– 4 h and silica was separated by centrifuging for 3 min at 10,000 RPM. The supernatant was separated and extracted with equal volume of ethyl acetate by shaking at 150 rpm and 30 C for 60 min. Then the mixture was centrifuged at 10,000 RPM for 30 min and the organic layer was collected and dried at 40 C. Afterwards, the sample was dissolved into the minimum volume of DMSO and the 40 μl of it was used for assaying the lipase inhibition activity. Pancreatic

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lipase corresponding to the 20 units was pre-incubated with the extract of the blue spot for 60 min at 37 C before adding the substrate. The percentage of residual activity of the lipase was determined by the spectrophotometric assay described below. Here, PNPB (200 lM) was employed as the lipase substrate and the reaction was maintained at 37 C for 30 min and the release of p-Nitrophenol was measured at 410 nm. The enzyme activity was detected as the μ moles of p-Nitrophenol released per minute. Orlistat was used as a positive control in the assay and the percent of enzyme inhibition was calculated with reference to the control that has solvent instead of extract [10]. With porcine pancreatic lipase (Sigma), water in dimethyl sulfoxide, Time= 0.5h, T= 37 °C , pH= 7.7, Enzymatic reaction, Reagent/catalyst Bayineni, Venkata Krishna; Suresh, Sukrutha; Singh, Gurmeet; Kadeppagari, Ravi-Kumar; Biochemical and Biophysical Research Communications; vol. 453; nb. 4; (2014); p. 784 - 786 View in Reaxys With truncated Candida antarctica lipase A, water in acetonitrile, pH= 7.6, Enzymatic reaction, Kinetics, Reagent/ catalyst Wikmark, Ylva; Engelmarkcassimjee, Karim; Lihammar, Richard; Bäckvall, Jan-E.; ChemBioChem; vol. 17; nb. 2; (2016); p. 141 - 145 View in Reaxys The temporal velocity profile was investigated for all four enzyme-powered pumps over both short and long time intervals. In case of catalase, fluid pumping was monitored for a time duration of 10 mins, at a distance of 50-100 jim away from the enzyme pattern and time intervals of 1 mm. No significant change in velocity of tracer particles was observed at each of the three different concentrations of hydrogen peroxide —10 mM, 50 mM, and 100 mM within the 10 mm time frame. Similar time-dependent studies of pumping speedwith urease in 0.75 M urea, GOx in 1 M glucose, and lipase in 0.5 M 4-nitrophenyl butyrateshowed no appreciable change in pumping velocity at short time intervals (FIG. 9). As expected, over longer time scales, the pumping velocity decreases. As the substrate is consumed, the reaction rate decreases, thereby slowing the fluid pumping speed. This wasdemonstrated with catalase in presence of 0.050 M of hydrogen peroxide at regular time intervals of 30 mins, for a duration of 4 h (FIG. 3a). Similar behavior was observed with urease-powered pumps in the presence of 1 M urea (FIG. 11). Significantly, these pumps can be recharged by introducing fresh substrate solution, after the initial substrate solution is exhausted and fluid pumping stops (FIG. 12). For both catalase and urease, fluid pumpingresumed with a velocity similar to that observed previously at that specific substrate concentration. With lipase, Enzymatic reaction Patent; THE PENN STATE RESEARCH FOUNDATION; Sen, Ayusman; Sengupta, Samudra; Patra, Debabrata; Ortiz-Rivera, Isamar; (32 pag.); US2017/65728; (2017); (A1) English View in Reaxys

O O

Rx-ID: 5320403 View in Reaxys 5/804 Yield 52 % Spectr., 35 % Spectr.

Conditions & References With sodium bromate, potassium hydrogensulfate in water, Time= 48h, T= 25 - 30 °C , Oxidation Metsger, Leonid; Bittner, Shmuel; Tetrahedron; vol. 56; nb. 13; (2000); p. 1905 - 1910 View in Reaxys

43 %Chro- With tert.-butylhydroperoxide, C60H66N18*3Fe(2+)*3O4S(2-) in water, acetonitrile, Time= 24h, T= 60 °C mat., 29 %Chromat. Mettry, Magi; Moehlig, Melissa Padilla; Gill, Adam D.; Hooley, Richard J.; Supramolecular Chemistry; vol. 29; nb. 2; (2017); p. 120 - 128 View in Reaxys

HO O

Rx-ID: 177008 View in Reaxys 6/804 Yield

Conditions & References With hydrogen, bei der Einw. von Enzympraeparaten aus Clostridium kluyveri

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Stadtman; Barker; Journal of Biological Chemistry; vol. 181; (1949); p. 223 - 235 View in Reaxys 98 %Chromat.

With [{CyPN(H)P}Co(CH2SiMe3)]-BArF 4, isopropyl alcohol in tetrahydrofuran, Time= 48h, T= 100 °C , Schlenk technique, Inert atmosphere Zhang, Guoqi; Yin, Zhiwei; Tan, Jiawen; RSC Advances; vol. 6; nb. 27; (2016); p. 22419 - 22423 View in Reaxys

HO OH

O O

Rx-ID: 845498 View in Reaxys 7/804 Yield 2.5 %, 91.5 %

Conditions & References With sodium bromate, Ru2(dmnapy)Cl4, Time= 0.25h, Ambient temperature Boelrijk, Alexandra E. M.; Neenan, Thomas X.; Reedijk, Jan; Journal of the Chemical Society - Dalton Transactions; nb. 23; (1997); p. 4561 - 4570 View in Reaxys

67 %, 23 %

With C30H24N2O7W, dihydrogen peroxide in water, acetonitrile, Time= 14h, Reflux Maiti, Swarup K.; Dinda, Subhajit; Banerjee, Surajit; Mukherjee, Alok K.; Bhattacharyya, Ramgopal; European Journal of Inorganic Chemistry; nb. 12; (2008); p. 2038 - 2051 View in Reaxys

16 %, 53 %

With tert.-butylhydroperoxide, tetra-tert-butoxychromium in benzene, Time= 24h, T= 20 °C Stepovik; Zaburdaeva; Fukin; Karaghiosoff; Russian Journal of General Chemistry; vol. 85; nb. 11; (2015); p. 2547 - 2559; Zh. Obshch. Khim.; vol. 85; nb. 11; (2015); p. 1805 - 1817,13 View in Reaxys With air, copper, T= 270 °C Mailhe; de Godon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 517; Bulletin de la Societe Chimique de France; vol. <4> 27; (1920); p. 333 View in Reaxys With 2,2,6,6-tetramethyl-1-oxo-piperidinium; GENERIC INORGANIC ANION in acetonitrile, T= 10 °C , Product distribution, Kinetics Ganiev; Suvorkina; Igoshina; Kabal'nova; Imashev; Tolstikov; Russian Chemical Bulletin; vol. 51; nb. 6; (2002); p. 982 - 985 View in Reaxys With oxygen, potassium carbonate, PVP-stabilized 1:3 Au:Pd nanoparticles in water, T= 61.84 °C , p= 760.051Torr , Product distribution, Kinetics Hou, Wenbo; Dehm, Nicole A.; Scott, Robert W.J.; Journal of Catalysis; vol. 253; nb. 1; (2008); p. 22 - 27 View in Reaxys With oxygen, sodium acetate in water, Time= 24h, T= 130 °C , Autoclave Wang, Liang; Meng, Xiangju; Wang, Bin; Chi, Wenyang; Xiao, Feng-Shou; Chemical Communications; vol. 46; nb. 27; (2010); p. 5003 - 5005 View in Reaxys With Pt/γ-Al2O3, oxygen in water, Time= 5h, T= 90 °C , p= 750.075Torr , Autoclave, Reagent/catalyst, Time Lu, Tianliang; Du, Zhongtian; Liu, Junxia; Ma, Hong; Xu, Jie; Green Chemistry; vol. 15; nb. 8; (2013); p. 2215 2221 View in Reaxys With 1-methyl-2-azaadamantane-N-oxyl, NaClO, sodium hydrogencarbonate in water, acetonitrile, pH= 10, Electrochemical reaction, Catalytic behavior, Kinetics, Reagent/catalyst

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Rafiee, Mohammad; Miles, Kelsey C.; Stahl, Shannon S.; Journal of the American Chemical Society; vol. 137; nb. 46; (2015); p. 14751 - 14757 View in Reaxys 2.6 General Procedure for Solvent-Free Aerobic Oxidation of Alcohols General procedure: Oxidation of alcohols with palladium nanoparticles supported on PE-HBPE was performed using molecular oxygen in the absence of solvent. For this purpose, 5.0 mg of the catalyst was dispersed in alcohol (5.0 ml) in a three necked round flask with a reflux condenser under stirring. Oxygen flow was bubbled at a flow-rate of 20 ml/min. After the allowed reaction time duration, the catalyst was removed from the mixture, and the products were analyzed using gas chromatography. With oxygen in neat (no solvent), Time= 5h, T= 65 °C , Reagent/catalyst, Overall yield = 78 percent Mahdavi, Hossein; Sahraei, Razieh; Catalysis Letters; vol. 146; nb. 5; (2016); p. 977 - 990 View in Reaxys With oxygen in water, Time= 6h, T= 100 °C , p= 2250.23Torr Gandarias, Inaki; Nowicka, Ewa; May, Blake J.; Alghareed, Shaimaa; Armstrong, Robert D.; Miedziak, Peter J.; Taylor, Stuart H.; Catalysis Science and Technology; vol. 6; nb. 12; (2016); p. 4201 - 4209 View in Reaxys

Rx-ID: 845513 View in Reaxys 8/804 Yield 76 %, 5 %

Conditions & References With sodium bromate, sodium hydrogensulfite, Time= 2h, Ambient temperature Takase, Kiyoshi; Masuda, Haruyoshi; Kai, Osamu; Nishiyama, Yutaka; Sakaguchi, Satoshi; Ishii, Yasutaka; Chemistry Letters; nb. 10; (1995); p. 871 - 872 View in Reaxys

76 %, 5 %

With sodium bromate, sodium hydrogensulfite, Time= 2h, Ambient temperature, other primary alcohols and α,ω-diols, var. solvents, temp. and time, Product distribution, Mechanism Takase, Kiyoshi; Masuda, Haruyoshi; Kai, Osamu; Nishiyama, Yutaka; Sakaguchi, Satoshi; Ishii, Yasutaka; Chemistry Letters; nb. 10; (1995); p. 871 - 872 View in Reaxys

5 %, 76 %

With sodium bromate, sodium hydrogensulfite, Time= 2h, Ambient temperature Takase, Kiyoshi; Masuda, Haruyoshi; Kai, Osamu; Nishiyama, Yutaka; Sakaguchi, Satoshi; Ishii, Yasutaka; Chemistry Letters; nb. 10; (1995); p. 871 - 872 View in Reaxys

70 %, 22 %

38 : Example 38 Dehydrogenative Synthesis Reaction for Carboxylic Acid from Lower Alcohol and Water as StartingMaterials General procedure: A catalytic reaction for obtaining hydrogen at the same time as obtaining, using a mixture of a lower alcohol (ethanol, 1 -propanol, 1 -butanol) and water as starting materials, a carboxylic acid having the corresponding number of carbons was examined. First, anionic catalyst 3 (3.0 mol percent) and sodium hydroxide (3.0 mol percent) were added to a mixture of ethanol (10 mmol) and water (20 mmol), and when a reaction was carried out under reflux conditions for 20 hours acetic acid was formed at a yield of 85percent, and 445 mE (yield 92percent) of hydrogen was also obtained (entry 1). When a similar reaction using a mixture of 1 -propanol and water as starting materials was carried out over 40 hours, propionic acid was obtained at a yield of 68percent, and 411 mE (yield 85percent)progressed, and butyric acid could be obtained accompanied by the generation of hydrogen (entries 3 and 4). With C20H22IrN2O3 (1-)*Na(1+), sodium hydroxide in water, Time= 40h, Reflux, Inert atmosphere, Time Patent; Kanto Kagaku Kabushiki Kaisha; Yamaguchi, Ryohei; Fujita, Ken-ichi; (26 pag.); US2016/297844; (2016); (A1) English View in Reaxys

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With cerium (IV) sulfate, sulfuric acid, bei der elektrochemische Oxydation an Bleianoden Radtschenko; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 10; (1937); p. 683; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 13; (1940); p. 1348; ; (1941); p. 2469; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 294 View in Reaxys Radtschenko; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 13; (1940); p. 1348; ; (1941); p. 2469 View in Reaxys With PEG-1000, supercritical CO2, oxygen, [Pd561phen60(OAc)180], Time= 4h, T= 80 °C Hou, Zhenshan; Theyssen, Nils; Brinkmann, Axel; Leitner, Walter; Angewandte Chemie - International Edition; vol. 44; nb. 9; (2005); p. 1346 - 1349 View in Reaxys 87 %Chro- With water, bromine, T= 20 °C , Reagent/catalyst mat., 8 %Chromat. Nikishin; Sokova; Terent´ev; Kapustina; Russian Chemical Bulletin; vol. 64; nb. 12; (2015); p. 2845 - 2850; Izv. Akad. Nauk, Ser. Khim.; nb. 12; (2015); p. 2845 - 2850,6 View in Reaxys

O C

HO O

Rx-ID: 1895070 View in Reaxys 9/804 Yield 51 %, 9 %

Conditions & References General procedure: The hydrocarboxylation experiments were performed following the previously developed protocol [31–35]. The reaction mixtures were placed into a 13.0-mL stainless steel autoclave, equipped with a Teflon-coated magnetic stirring bar. Then the autoclave was closed and flushed with CO three times for removing the air and finally pressurized with CO (CAUTION: due to the toxicity of CO, the heating oven should be located in a well-ventilated hood.) The reaction mixture was stirred using a magnetic stirrer and an oil bath, whereupon it was cooled in an ice bath, degassed, opened and the contents transferred to a flask. Diethyl ether and cycloheptanone (GC internal standard) were added. The obtained mixture was vigorously stirred for 10 min, and the organic layer was analyzed typically by GC [a Fisons Instruments GC 8000 series gas chromatograph equipped with30 m×0.22 mm×25 μm, BP20 (SGE) capillary column (helium was the carrier gas) With pyrazinecarboxylic acid, dipotassium peroxodisulfate, ferrocene in water, acetonitrile, Time= 4h, T= 60 °C , p= 7600.51Torr , Autoclave, Overall yield = 60 percent Shul'pin, Georgiy B.; Kirillova, Marina V.; Shul'pina, Lidia S.; Pombeiro, Armando J.L.; Karslyan, Eduard E.; Kozlov, Yuriy N.; Catalysis Communications; vol. 31; (2013); p. 32 - 36 View in Reaxys

41.9 %, 5.2 %

With dipotassium peroxodisulfate, BF4 (1-)*C24H51BCu3N3O16 (1+)*2H2O, water in acetonitrile, Time= 6h, T= 60 °C , Autoclave Kirillov, Alexander M.; Karabach, Yauhen Y.; Kirillova, Marina V.; Haukka, Matti; Pombeiro, Armando J. L.; Dalton Transactions; vol. 40; nb. 24; (2011); p. 6378 - 6381 View in Reaxys

40.5 %, 6.2 %

With dipotassium peroxodisulfate, C26H38Cu3N4O16, water in acetonitrile, Time= 6h, T= 60 °C , Autoclave, Green chemistry, Reagent/catalyst Ansari, Istikhar A.; Sama, Farasha; Raizada, Mukul; Shahid; Ahmad, Musheer; Siddiqi, Zafar A.; New Journal of Chemistry; vol. 40; nb. 11; (2016); p. 9840 - 9852 View in Reaxys

1.7 % Chromat., 7.5 % Chromat.

With palladium diacetate, dipotassium peroxodisulfate, copper dichloride in trifluoroacetic acid, Time= 20h, T= 80 °C Miyata, Tsutomu; Nakata, Kazuyuki; Yamaoka, Yoshinori; Taniguchi, Yuki; Takaki, Ken; Fujiwara, Yuzo; Chemistry Letters; nb. 6; (1993); p. 1005 - 1008 View in Reaxys

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With dipotassium peroxodisulfate, dipropionatopalladium(II), copper(II) sulfate in trifluoroacetic acid, T= 80 °C , p= 15200Torr , Yield given. Yields of byproduct given. Title compound not separated from byproducts Nishiguchi, Takahiro; Nakata, Kazuyuki; Takaki, Ken; Fujiwara, Yuzo; Chemistry Letters; nb. 7; (1992); p. 1141 1142 View in Reaxys 6.7 % Chromat., 2.3 % Chromat.

With palladium diacetate, dipotassium peroxodisulfate, copper diacetate in trifluoroacetic acid, Time= 20h, T= 80 °C

6.7 % Chromat., 2.3 % Chromat.

With palladium diacetate, dipotassium peroxodisulfate, copper diacetate in trifluoroacetic acid, Time= 20h, T= 80 °C , var. catalysts, var. ratio of catalysts, Product distribution

Miyata, Tsutomu; Nakata, Kazuyuki; Yamaoka, Yoshinori; Taniguchi, Yuki; Takaki, Ken; Fujiwara, Yuzo; Chemistry Letters; nb. 6; (1993); p. 1005 - 1008 View in Reaxys

Miyata, Tsutomu; Nakata, Kazuyuki; Yamaoka, Yoshinori; Taniguchi, Yuki; Takaki, Ken; Fujiwara, Yuzo; Chemistry Letters; nb. 6; (1993); p. 1005 - 1008 View in Reaxys With dipotassium peroxodisulfate, copper dihydrocarbonate, palladium, trifluoroacetic acid, Time= 20h, T= 80 °C , p= 15200Torr , var. Pd-Cu-based catalyst system, Product distribution Nakata, Kazuyuki; Miyata, Tsutomu; Taniguchi, Yuki; Takaki, Ken; Fujiwara, Yuzo; Journal of Organometallic Chemistry; vol. 489; nb. 1-2; (1995); p. 71 - 76 View in Reaxys 9 :In a typical experiment the reaction mixtures were prepared as follows. To a 13.0 mL stainless steel autoclave, equipped with a Teflon-coated magnetic stirring bar, were added 0-32.0 μmol (typically 8.0 μmol) of catalyst (optional), 1.00-2.00 mmol (typically 1.50 mtnol) <n="10"/>of K2S2O8, 2.0-3.0 mL of H2O, 2.0-4.0 mL of MeCN and 1.001.50 mmol (typically 1.00 mmol) of liquid alkane (in the case of pentane, cyclopentane, hexane and cyclohexane) . Then the autoclave was closed and flushed with dinitrogen three times for removing the air and pressurized with 20-40 atm (typically 20 atm) of carbon monoxide. In the case of using a gaseous alkane (ethane, propane or π-butane) , the reactor had been pressurized with 1-10 atm of this gas prior to the admission of CO. The reaction mixture was vigorously stirred for 2-6 h at 25-60 0C using a magnetic stirrer and an oil bath, whereupon it was cooled in an ice bath, degassed, opened and transferred to a Schlenk tube. Diethyl ether (9.0-11.0 mL) , to separate from the inorganic compounds, and cycloheptanone (90 μL, internal standard) were added. The obtained mixture was vigorously stirred and the organic layer was analyzed by gas chromatography (internal standard method) using a Fisons Instruments GC 8000 series gas chromatograph with a DB WAX fused silica capillary column (P/N 123-7032) and the Jasco-Borwin v.1.50 software. In some cases, the products were also identified by GC-MS, 1H and 13C-(1Hj NMR techniques, using a Trio 2000Fisons spectrometer with a coupled Carlo Erba(Auto/HRGC/MS) gas chromatograph, and a Varian UNITY 300NMR spectrometer, respectively. The catalysts have been obtained either according to the previously described methods t3a'4a'12] or from commercial sources.Examples of effects on the alkane carboxylation of various factors, such as the relative amounts of alkane, <n="11"/>carbon monoxide, oxidant, solvent and its composition, catalyst type and reaction temperature, are listed in Tables 1 and 2 and discussed below.2 - Examples; The carboxylation of alkanes typically proceeds more efficiently in the presence of a metal catalyst, thus leading to higher yields of carboxylic acids which can usually be achieved in a shorter reaction time and at lower reaction temperature, in comparison with the same reaction performed in the absence of catalyst.The tetracopper triethanolaminate complex [OeCu4(N(CH2CH2O)3J4(BOH)4] [BF4] 2 exhibits the highest level of activity among the tested catalysts (Table 2) . For this catalyst, the maximum overall yields for the various alkanes are in the following order: cyclohexanecarboxylic acid from cyclohexane {ca. 72percent, example 15) , 2- methylhexanoic and 2-ethylpentanoic acids from rzhexane(ca. 45percent, example 14), isobutyric and butyric acids from propane {ca. 38percent, example 9), 2-methylbutanoic acid from n- butane [ca. 30percent, example 10) , 2-meth.ylpentanoic and 2- ehtylbutanoic acids from npentane (ca.. 23percent, example 11) , cyclopentanecarboxylic acid from cyclopentane (ca. 22percent, example 12), and propionic acid from ethane (ca. 9percent, example 8) . The yields based on the peroxodisulphate oxidant are also high, being typically h, of those based on alkane; Other catalysts, namely [Cu2 (H2tea) 2{ C5H4 (COO) 2- l, 4}]n-2ωH2O, [Cu(H2tea) (N3)] , Cu (NO3) 2 .bul. 2.5H2O,Ca[V(ON(CH2COO)2J2] , K2Cr2O7, MnO2 and Fe (OH) 3 .bul. 0.5H2O, can also be applied for the carboxylation of e.g. cyclohexane <n="14"/>leading to yields of cyclohexanecarboxylic acid in the 14-39percent range (Table 2, examples 17-23) .The catalyst amount has only a slight effect on the product yield, but lower catalyst amounts lead to quite higher TONs. For example, in the case of cyclopentane carboxylation, a catalyst amount decrease from 8.0 to 2.0 μmol leads only to a slight yield lowering from 22.2 to20.5percent, whereas the TON increases from 42 to 153 (Table 2, examples 12 and 13) .In both metal-free and metal-catalysed processes the secondary carbon atom in alkanes is more easily carboxylated favouring the formation of

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branched carboxylic acids. Moreover, the partial oxidation of linear alkanes to carboxylic acids (typically occurring in TFA containing systems) or to alcohols and ketones does not proceed, to a considerable extent, in our processes.The efficiency of both metal-free and metal- catalysed processes for alkane carboxylation is dependent on various factors, namely the amount and composition of solvent mixture (the 1:1 or 1:2 H2O/MeCN volumetric ratio usually is very favourable but not an exclusive one) , and the CO pressure (the highest yields and selectivities are commonly achieved for the typical CO pressure of 20 atm) . Nevertheless, other factors such as the type and amount of catalyst, oxidant amount, relative amounts of all the reaction components and reaction time, also influence the obtained results. With dipotassium peroxodisulfate, water, [OCu4{N(CH2CH2O)3}4(BOH)4][BF4]2 in acetonitrile, Time= 6h, T= 60 °C , p= 25081.7Torr , Product distribution / selectivity Patent; INSTITUTO SUPERIOR TECNICO; WO2008/88234; (2008); (A1) English View in Reaxys With dipotassium peroxodisulfate, 2BF4 (1-)*C24H52B4Cu4N4O17 (2+), water in acetonitrile, Time= 6h, T= 60 °C , p= 17481.2Torr , Autoclave Kirillova, Marina V.; Kirillov, Alexander M.; Kuznetsov, Maxim L.; Silva, Jose A. L.; Frausto Da Silva, Joao J. R.; Pombeiro, Armando J. L.; Chemical Communications; nb. 17; (2009); p. 2353 - 2355 View in Reaxys 52.7 With dipotassium peroxodisulfate, 2BF4 (1-)*C24H52B4Cu4N4O17 (2+), water in acetonitrile, Time= 6h, T= 60 °C , Auto%Chroclave mat., 5.6 %Chromat. Kirillova, Marina V.; Kirillov, Alexander M.; Pombeiro, Armando J.L.; Chemistry - A European Journal; vol. 16; nb. 31; (2010); p. 9485 - 9493 View in Reaxys

HO O

Rx-ID: 2919311 View in Reaxys 10/804 Yield

Conditions & References With sodium hydroxide in ethanol, Time= 0.416667h, ΔH, Thermodynamic data Wiberg, Kenneth B.; Waldron, Roy F.; Journal of the American Chemical Society; vol. 113; nb. 20; (1991); p. 7697 - 7705 View in Reaxys

75 (unit not With Horse Liver Esterase as Acetonic Powder, iPrO2CnPr in water, other enzyme (PPL), other ester, enzymatic disgiven) crimination of esters, Product distribution Jeso, B. De; Drouillard, S.; Degueil-Castaing, M.; Saux, A.; Maillard, B.; Synthetic Communications; vol. 18; nb. 14; (1988); p. 1691 - 1698 View in Reaxys 65 % Chromat.

With phosphate buffer, ethyl pivalate, pig pancreatic lipase, Ethyl isobutyrate in water, enzymatic discrimination of esters, Product distribution Jeso, B. De; Drouillard, S.; Degueil-Castaing, M.; Maillard, B.; Synthetic Communications; vol. 18; nb. 14; (1988); p. 1699 - 1706 View in Reaxys With sodium hydroxide, water, T= 80 °C , other temperature, Kinetics Buhse; Lavabre; Nagarajan; Micheau; Journal of Physical Chemistry A; vol. 102; nb. 51; (1998); p. 10552 - 10559 View in Reaxys With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid, esterase from Streptomyces diastatochromogenes in water, T= 25 °C , pH= 7.20, Enzyme kinetics

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Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid, esterase from Pseudomonas fluorescens in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid, lipase from Ophiostoma piliferum in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid, lipase from Bacillus thermocatenulanatus in water, T= 40 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With lipase from Pseudozyma hubeiensis SY62, water Park, Seongsoon; Bulletin of the Korean Chemical Society; vol. 37; nb. 10; (2016); p. 1720 - 1723 View in Reaxys

O O

HO O

Rx-ID: 4946121 View in Reaxys 11/804 Yield 92 %

Conditions & References 2.4. Catalytic tests General procedure: The heterogeneous catalysts, stored under ambient conditions,were used for catalytic reactions without any pretreatment. Typically,ester (1 mmol), 1 mL H2O and 10 mg of catalysts and a magneticstarter bar were added to a reaction vessel (Pyrex pressuretube, 13 mL), and the mixture was heated at 130 °C under air withstirring at 300 rpm. For the catalytic tests in Table 1 and kineticstudy, conversions and yields were determined by GC-FID usingn-dodecane as an internal standard as follows. After completionof the reaction, acetone (7 mL) was added to the mixture, andthe catalyst was separated by centrifugation. Then, n-dodecane(0.2 mmol) was added to the reaction mixture, and the mixturewas analyzed by GC-FID and GC-MS. The GC-FID sensitivities ofthe products were determined using commercial carboxylic acidsor the isolated products after the reaction. For some of the productsin Tables 2 and 3, we determined isolated yields of the carboxylicacids as follows. After the filtration of the catalyst, followed bywashing the catalyst with acetone (6 mL), and by evaporation,the product was isolated by column chromatography using silicagel 60 (spherical, 63-210 μm, Kanto Chemical Co. Ltd.) with hexane/ethyl acetate (60/40-80/20) as the eluting solvent, followedby analyses by 1H NMR, 13C NMR and GC-MS equipped with thesame column as GC-FID. With octadecyltriethoxysilane-treated high-silica Hβ-20 zeolite in water, Time= 24h, T= 130 °C , Reagent/catalyst Siddiki; Toyao, Takashi; Kon, Kenichi; Touchy, Abeda S.; Shimizu, Ken-ichi; Journal of Catalysis; vol. 344; (2016); p. 741 - 748 View in Reaxys With PIPES buffer, Candida rugosa lipase in water, toluene, other enzymes, other solvent, Rate constant Um, Pil-Je; Drueckhammer, Dale G.; Journal of the American Chemical Society; vol. 120; nb. 23; (1998); p. 5605 5610

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View in Reaxys With Candida antarctica lipase B, 4-nitro-phenol, MOPS buffer in water, T= 25 °C , pH= 7.2, Enzymatic reaction, Enzyme kinetics, Further Variations: Reagents Magnusson; Hult; Holmquist; Journal of the American Chemical Society; vol. 123; nb. 18; (2001); p. 4354 - 4355 View in Reaxys With roots of Manihot dulcis in water, T= 20 °C , Kinetics, Further Variations: Reagents Machado, Luciana L.; Souza, Joao Sammy N.; de Mattos, Marcos Carlos; Sakata, Solange K.; Cordell, Geoffrey A.; Lemos, Telma L.G.; Phytochemistry; vol. 67; nb. 15; (2006); p. 1637 - 1643 View in Reaxys With REBr enzyme, water, T= 40 °C , pH= 8.5, Enzymatic reaction, Kinetics, Concentration Beloqui, Ana; Polaina, Julio; Vieites, Jose Maria; Reyes-Duarte, Dolores; Torres, Rodrigo; Golyshina, Olga V.; Chernikova, Tatyana N.; Waliczek, Agnes; Aharoni, Amir; Yakimov, Michail M.; Timmis, Kenneth N.; Golyshin, Peter N.; Ferrer, Manuel; ChemBioChem; vol. 11; nb. 14; (2010); p. 1975 - 1978 View in Reaxys With Rhodococcus sp. LKE-028 esterase, T= 70 °C , pH= 11, aq. buffer, Enzymatic reaction Kumar, Lokendra; Singh, Balvinder; Adhikari, Dilip Kumar; Mukherjee, Joydeep; Ghosh, Debashish; Process Biochemistry; vol. 47; nb. 6; (2012); p. 983 - 991 View in Reaxys With lipases from Rhizomucor miehei immobilized on octyl-agarose in aq. phosphate buffer, pH= 7, Enzymatic reaction Bavaro, Teodora; Torres-Salas, Pamela; Ubiali, Daniela; Terreni, Marco; RSC Advances; vol. 3; nb. 20; (2013); p. 7355 - 7359 View in Reaxys O O

O O

HO O

Rx-ID: 8746804 View in Reaxys 12/804 Yield

Conditions & References With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid, esterase from Pseudomonas fluorescens in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid, esterase from Streptomyces diastatochromogenes in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid, lipase from Bacillus thermocatenulanatus in water, T= 40 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556

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View in Reaxys With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid, lipase from Ophiostoma piliferum in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Lipomax enzyme in hexane, Time= 0.0666667 - 0.5h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys With Lecitasereg; Ultra, water, calcium chloride, Time= 0.333333h, T= 30 °C , pH= 8.5, aq. buffer, Enzymatic reaction Mishra, Mithilesh Kumar; Kumaraguru, Thenkrishnan; Sheelu, Gurrala; Fadnavis, Nitin W.; Tetrahedron Asymmetry; vol. 20; nb. 24; (2009); p. 2854 - 2860 View in Reaxys

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With recombinant Fusarium solani pisi cutinase, water, Time= 0.25h, T= 37 °C , pH= 8, aq. phosphate buffer, Enzymatic reaction Chen, Sheng; Su, Lingqia; Billig, Susan; Zimmermann, Wolfgang; Chen, Jian; Wu, Jing; Journal of Molecular Catalysis B: Enzymatic; vol. 63; nb. 3-4; (2010); p. 121 - 127 View in Reaxys With water, Candida rugosa lipase, Time= 0.5h, T= 35 °C , pH= 7, phosphate buffer, Kinetics, Reagent/catalyst Bayramoglu, Guelay; Hazer, Baki; Altintas, Begum; Arica, M. Yakup; Process Biochemistry; vol. 46; nb. 1; (2011); p. 372 - 378 View in Reaxys With Psychrobacter sp. TA144 lipase, recombinant, containing MPILPV sequence at N-terminal, apparent molecular mass: ca. 48000 Da in acetonitrile, T= 35 °C , pH= 8, aq. buffer, Enzymatic reaction, Kinetics De Santi, Concetta; Tutino, Maria Luisa; Mandrich, Luigi; Giuliani, Maria; Parrilli, Ermenegilda; Del Vecchio, Pompea; de Pascale, Donatella; Biochimie; vol. 92; nb. 8; (2010); p. 949 - 957 View in Reaxys With water, pH= 7, aq. Kpi buffer, Enzymatic reaction Ferrario, Valerio; Ebert, Cynthia; Knapic, Lorena; Fattor, Diana; Basso, Alessandra; Spizzo, Patrizia; Gardossi, Lucia; Advanced Synthesis and Catalysis; vol. 353; nb. 13; (2011); p. 2466 - 2480 View in Reaxys With bovine pancreatic bile-salt-activated lipase, water, tris hydrochloride, sodium taurocholate, sodium chloride, T= 25 °C , pH= 7, Enzymatic reaction, Kinetics, Reagent/catalyst Chahinian, Henri; Fantini, Jacques; Garmy, Nicolas; Manco, Giuseppe; Sarda, Louis; Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids; vol. 1801; nb. 11; (2010); p. 1195 - 1204 View in Reaxys Stage 1: With pancreatin, sodium cholate, sodium cholate, sodium chloride, calcium chloride, Time= 1h, T= 37 °C , pH= 6.5 - 7.2, Trizma-maleate buffer Stage 2: With hydrogenchloride in water Martin, Diana; Moran-Valero, Maria I.; Senorans, Francisco J.; Reglero, Guillermo; Torres, Carlos F.; Lipids; vol. 46; nb. 3; (2011); p. 277 - 285 View in Reaxys 2.7.2. Tributyrin activity The hydrolysis of tributyrin measures lipase activity by the liberation of butyric acid. The reaction was monitored titrimetrically in a Mettler DL50 pH-stat, using 100 mM sodium hydroxide. A 48.5 mL potassium phosphate buffer solution (10 mM, pH 7.0) was incubated in a thermostated vessel at 25 °C and stirred sufficiently. Then, 1.47 mL tributyrin were added and the pH-stat was started to keep the pH at 7.0. When the pH stabilizes, 5 mg catalyst were added and the consumption of NaOH was determined. One lipase unit corresponds to consumption of 1 μmol NaOH/min. With sodium hydroxide in aq. phosphate buffer, T= 25 °C , pH= 7.0, Enzymatic reaction, Kinetics, Reagent/catalyst Fernandez, Oscar; Diaz, Isabel; Torres, Carlos F.; Tobajas, Montserrat; Tejedor, Victor; Blanco, Rosa M.; Applied Catalysis A: General; vol. 450; (2013); p. 204 - 210 View in Reaxys 2.10. Substrate specificity and kinetics parameters General procedure: The substrate specificity for synthetic triacylglycerol esters was analyzed titrimetrically using 10 mM NaOH for titration according to the method of Egger et al. [37]. The substrates at a concentration of 10 mM were emulsified in 20 ml phosphate buffer (2.5 mM, pH 6.5) containing 1percent arabic gum. The reaction was initiated with 10 μl of suitably diluted enzyme, and incubated at 50 °C for 10 min, after which the reaction was titrated and the amount of consumed NaOH recorded. One unit of enzyme activity was defined as the amount of enzyme required to release 1.0 μmol of pNP or fatty acid per minute under the above assay conditions. With recombinant esterase from Rhizomucor miehei in aq. phosphate buffer, Time= 0.166667h, T= 50 °C , pH= 6.5, Enzymatic reaction, Catalytic behavior

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Yan, Qiao-Juan; Yang, Shao-Qing; Duan, Xiao-Jie; Xu, Hai-Bo; Liu, Yu; Jiang, Zheng-Qiang; Journal of Molecular Catalysis B: Enzymatic; vol. 109; (2014); p. 76 - 84 View in Reaxys General procedure: The esterase activity was determined using p-nitrophenyl esters as substrates [7,8]. The lipolytic activity was evaluated titrimetrically using triacylglycerols with fatty acids of various chain lengths as substrates. 1 vol. of a certain triglyceride and 6 vol. of 2.0percent (w/v) polyvinyl alcohol in 50mM glycine-NaOH buffer (pH 9.0) were mixed in a blender (10,000rpm) until homogeneity was achieved. Then, 9mL of this emulsified triglyceride was incubated with 1mL of suitably diluted enzyme at 35°C for 10min and terminated by the addition of 15mL of ethanol. The release of fatty acids was monitored by titration using 50mM NaOH. One unit of lipolytic activity was defined as the amount of lipase necessary to produce 1μmol of fatty acid per minute under the above conditions. Interfacial activation was detected using p-nitrophenyl butyrate in a concentration range of 0.5–4.0mM. The temperature optima were determined under the conditions stated above, except that the reaction temperatures ranged from 25 to 45°C. To detect thermostability, lipases were incubated at 30, 35, 40, 45, 50, and 55°C for 10min, respectively. After incubation, residual enzymatic activity was measured using tributyrin as the substrate. With Penicillium expansum lipase T66V/D70N mutant, polyvinyl alcohol in aq. buffer, Time= 0.166667h, T= 35 °C , pH= 9, Enzymatic reaction, Reagent/catalyst Tang, Lianghua; Su, Min; Yan, Junzhe; Xie, Sheng; Zhang, Wenhuang; Process Biochemistry; vol. 50; nb. 8; (2015); p. 1218 - 1223 View in Reaxys 6-3 : <6-3> Characteristics of phospholipase/lipase MPlaG over carbon length General procedure: The activity of MPlaG to hydrolyze triacylglyceride, olive oil, and phosphatidylcholine was measured by titrating free fatty acid using pH titrator (842 Tirando, Metrohm). By adding 10 mM NaOH solution, pH of the substrate emulsion was regulated to 8.0. Then, a proper amount of enzyme solution was added thereto. Execretion rate of fatty acid was measured by using pH titrator for 5 minutes. 1 unit of lipase activity was defined as the enzyme amount capable of releasing 1 µmole of fatty acid. To exclude the non-enzymatic hydrolysis value of the substrates, the activity was measured without enzyme addition for every measurement under different conditons, which would be the control reaction. (0084) As a result, specific enzyme activity of MPlaG toward olive oil and phosphatidylcholine was 2957±144 and 1735±147 Umg-1, respectively. MPlaG was a member of phospholipase family, but showed a significant lipase activity to olive oil. (0085) To further investigate specificity to substrate each having different carbon length, pH titration was performed with triacylglycerides sucha as tributyrin (C4), tricaprylin (C8), tricaprin (C10), trilaurin (C12), tripalmitin (C16), and triolein (C18:1). As a result, the highest enzyme activity was observed to tributyrin (C4) and the enzyme activity was significantly decreased as chain extended (Figure 9A). With phospholipase/lipase MPlaG, water, sodium hydroxide, pH= 8, Enzymatic reaction Patent; Korea Research Institute of Bioscience and Biotechnology; YOON, Jung-Hoon; LEE, Mi Hwa; KANG, Chul Hyung; OH, Ki Hoon; OH, Tae Kwang; (55 pag.); EP2784160; (2016); (B1) English View in Reaxys With water, pH= 7, Enzymatic reaction, Reagent/catalyst Kovalenko; Chuenko; Perminova; Rudina; Kinetics and Catalysis; vol. 57; nb. 3; (2016); p. 394 - 403; Kinet. Katal.; vol. 57; nb. 3; (2016); p. 398 - 408,11 View in Reaxys

Rx-ID: 22955693 View in Reaxys 13/804 Yield 24.0 %, 0.4 %, 2.3 %

Conditions & References 7 : EXAMPLE 7 EXAMPLE 7 In this example, n-butyl alcohol was reacted with oxygen over Pd on Zeolite Y. As expected, n-butyl butyrate was obtained in good yield with high selectivity. Changes and modifications in the specifically described embodiments can be carried out without departing from the scope of the invention, which is intended to be limited only by the scope of the appended claims. n-butyl alcohol conversion catalyzed by Pd on Zeolite YCatalyst: Pd on Zeolite YTemperature, ° C.: 110WHSV, W/W/ Hr.: 0.5Feed: n-butyl alcoholPressure, atm.: 2PRODUCTCOMPOSITIONn-butyl butyrate (wt percent)24.0n-butyl al-

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cohol (wt percent)61.8butyric acid (wt percent)0.4n-butyl aldehyde (wt percent)2.3H2O (wt percent)7.1Fuel gas (wt percent)3.0Total unidentified Species (wt percent)1.4 With oxygen, Pd on Zeolite Y, T= 110 °C , p= 1520.1Torr , Product distribution / selectivity Patent; Yan, Tsoung Y.; Chang, Jen-Ray; US6399812; (2002); (B1) English View in Reaxys 5.5 %Chromat., 5.2 %Chromat., 0.8 %Chromat.

With oxygen in carbon dioxide, Time= 8h, T= 80 °C , p= 135014Torr , Supercritical conditions Hou, Zhenshan; Theyssen, Nils; Brinkmann, Axel; Klementiev, Konstantin V.; Gruenert, Wolfgang; Buehl, Michael; Schmidt, Wolfgang; Spliethoff, Bernd; Tesche, Bernd; Weidenthaler, Claudia; Leitner, Walter; Journal of Catalysis; vol. 258; nb. 2; (2008); p. 315 - 323 View in Reaxys With oxygen in water, Time= 6h, T= 100 °C , p= 2250.23Torr Gandarias, Inaki; Miedziak, Peter J.; Nowicka, Ewa; Douthwaite, Mark; Morgan, David J.; Hutchings, Graham J.; Taylor, Stuart H.; ChemSusChem; vol. 8; nb. 3; (2015); p. 473 - 480 View in Reaxys With oxygen in water, Time= 6h, T= 100 °C , p= 2250.23Torr Gandarias, Inaki; Nowicka, Ewa; May, Blake J.; Alghareed, Shaimaa; Armstrong, Robert D.; Miedziak, Peter J.; Taylor, Stuart H.; Catalysis Science and Technology; vol. 6; nb. 12; (2016); p. 4201 - 4209 View in Reaxys O

O HO

HO O

Rx-ID: 41670127 View in Reaxys 14/804 Yield 70 %

Conditions & References With hydrogen, Time= 10h, T= 200 °C , p= 37503.8Torr , Autoclave Liu, Xiaoran; Wang, Xicheng; Xu, Guoqiang; Liu, Qiang; Mu, Xindong; Liu, Haichao; Journal of Materials Chemistry A; vol. 3; nb. 46; (2015); p. 23560 - 23569 View in Reaxys With hydrogen in 1,4-dioxane, Time= 4h, T= 119.84 °C , p= 60006Torr , Autoclave, Catalytic behavior, Reagent/ catalyst, Temperature, Overall yield = 26 percent Takeda, Yasuyuki; Tamura, Masazumi; Nakagawa, Yoshinao; Okumura, Kazu; Tomishige, Keiichi; Catalysis Science and Technology; vol. 6; nb. 14; (2016); p. 5668 - 5683 View in Reaxys O O

Rx-ID: 41812075 View in Reaxys 15/804 Yield

Conditions & References With truncated Candida antarctica lipase A, water, sodium hydroxide in acetonitrile, Time= 0.333333h, T= 37 °C , pH= 7.5, Enzymatic reaction, Kinetics, Reagent/catalyst Wikmark, Ylva; Engelmarkcassimjee, Karim; Lihammar, Richard; Bäckvall, Jan-E.; ChemBioChem; vol. 17; nb. 2; (2016); p. 141 - 145 View in Reaxys

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OH O

Rx-ID: 42425726 View in Reaxys 16/804 Yield

Conditions & References 2.6. General procedures of enzymatic transesterification Lipase powder (1.0 mg for CAL, 2.0 mg for PCL) was dissolved in500 μL of solvent in a 4 mL screw-top vial with a stir bar. Ethyl butyrate(110 μL, 0.83 mmol), 1-butanol (110 μL, 1.21 mmol), and 50 μLcyclooctane (internal standard) were added. The reaction mixture wasstirred at 323 K at 300 rpm in an oil bath. For measurement of initialreaction rate, a 100-μL aliquot of the reaction mixture was withdrawnat specified time intervals and extracted with four portions ofheptane. The organic phase was analyzed using an Agilent 7890A gaschromatograph equipped with an FID and a capillary column (HP-5,30 m × 0.32 mm × 0.25 μm) and operated with a 1:4 split ratio usinghelium as the carrier gas. The analysis was performed under the followingconditions: inlet port temperature 523 K and detector temperature573 K. The oven program consisted of an initial temperature of 313 K that was maintained for 1 min after which the temperature was increasedat a rate of 30 K/min to a final temperature of 523 K. With Pseudomonas cepacia lipase, water, T= 49.84 °C , Enzymatic reaction, Kinetics, Reagent/catalyst Ou, Guangnan; He, Biyan; Halling, Peter; Biochimica et Biophysica Acta - General Subjects; vol. 1860; nb. 7; (2016); p. 1404 - 1408 View in Reaxys Rx-ID: 42478266 View in Reaxys 17/804

Yield

Conditions & References 2.2. Activity tests General procedure: Activity tests were performed in a 190-ml stainless steel autoclave with an inserted glass vessel. The catalyst was put into an autoclave together with a spinner and an appropriate amount of water and heated at 473 K with 8 MPa H2 for 1 h for the reduction pretreatment. The stirring rate was 250 rpm. After the pretreatment, the autoclave was cooled down, and hydrogen was removed.Sorbitol (0.5 g, Wako Pure Chemical Industries, Ltd., 98percent) and n-decane (20 ml; Tokyo Chemical Industry Co. Ltd., 99percent) were put into the autoclave. HZSM-5 was also added when necessary. After sealing the reactor, the air content was purged by flushing three times with Ar (1 MPa, 99.99percent; Nippon Peroxide Co., Ltd.). The reactor was pressurized with Ar to 0.5–4.0 MPa at room temperature and then heated to set temperatures (443–473 K). The heating took about 1–1.5 h. After the temperature reached the set one, the temperature was kept for appropriate reaction time. The stirring rate was 500 rpm. After reaction, the reactor was cooled down by using ice bath and the gases were collected in a gas bag. The reaction mixture was separated into organic and aqueous phases. The autoclave contents were transferred to a vial, and the catalyst was separated by centrifugation and filtration. With prereduced 3 wtpercent Pt-Ir alloy particle covered with ReOx supported on silica in decane, water, Time= 24h, T= 179.84 °C , p= 3750.38Torr , Inert atmosphere, Autoclave Liu, Sibao; Okuyama, Yasuyo; Tamura, Masazumi; Nakagawa, Yoshinao; Imai, Akio; Tomishige, Keiichi; Catalysis Today; vol. 269; (2016); p. 122 - 131 View in Reaxys Rx-ID: 42478267 View in Reaxys 18/804

Yield

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With prereduced 3 wtpercent Pt-Ir alloy particle covered with ReOx supported on silica in decane, water, Time= 48h, T= 179.84 °C , p= 3750.38Torr , Inert atmosphere, Autoclave, Temperature Liu, Sibao; Okuyama, Yasuyo; Tamura, Masazumi; Nakagawa, Yoshinao; Imai, Akio; Tomishige, Keiichi; Catalysis Today; vol. 269; (2016); p. 122 - 131 View in Reaxys Rx-ID: 42478268 View in Reaxys 19/804 Yield

Conditions & References 2.2. Activity tests General procedure: Activity tests were performed in a 190-ml stainless steel autoclave with an inserted glass vessel. The catalyst was put into an autoclave together with a spinner and an appropriate amount of water and heated at 473 K with 8 MPa H2 for 1 h for the reduction pretreatment. The stirring rate was 250 rpm. After the pretreatment, the autoclave was cooled down, and hydrogen was removed.Sorbitol (0.5 g, Wako Pure Chemical Industries, Ltd., 98percent) and n-decane (20 ml; Tokyo Chemical Industry Co. Ltd., 99percent) were put into the autoclave. HZSM-5 was also added when necessary. After sealing the reactor, the air content was purged by flushing three times with Ar (1 MPa, 99.99percent; Nippon Peroxide Co., Ltd.). The reactor was pressurized with Ar to 0.5–4.0 MPa at room temperature and then heated to set temperatures (443–473 K). The heating took about 1–1.5 h. After the temperature reached the set one, the temperature was kept for appropriate reaction time. The stirring rate was 500 rpm. After reaction, the reactor was cooled down by using ice bath and the gases were collected in a gas bag. The reaction mixture was separated into organic and aqueous phases. The autoclave contents were transferred to a vial, and the catalyst was separated by centrifugation and filtration. With prereduced 3 wtpercent Pt modified Ir-ReOx supported on silica, HZSM-5 in decane, water, Time= 48h, T= 189.84 °C , p= 3750.38Torr , Inert atmosphere, Autoclave Liu, Sibao; Okuyama, Yasuyo; Tamura, Masazumi; Nakagawa, Yoshinao; Imai, Akio; Tomishige, Keiichi; Catalysis Today; vol. 269; (2016); p. 122 - 131 View in Reaxys Rx-ID: 42478271 View in Reaxys 20/804

Yield

HO HO

H H

OH OH OH

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Rx-ID: 42478272 View in Reaxys 21/804 Yield

Conditions & References 2.2. Activity tests General procedure: Activity tests were performed in a 190-ml stainless steel autoclave with an inserted glass vessel. The catalyst was put into an autoclave together with a spinner and an appropriate amount of water and heated at 473 K with 8 MPa H2 for 1 h for the reduction pretreatment. The stirring rate was 250 rpm. After the pretreatment, the autoclave was cooled down, and hydrogen was removed.Sorbitol (0.5 g, Wako Pure Chemical Industries, Ltd., 98percent) and n-decane (20 ml; Tokyo Chemical Industry Co. Ltd., 99percent) were put into the autoclave. HZSM-5 was also added when necessary. After sealing the reactor, the air content was purged by flushing three times with Ar (1 MPa, 99.99percent; Nippon Peroxide Co., Ltd.). The reactor was pressurized with Ar to 0.5–4.0 MPa at room temperature and then heated to set temperatures (443–473 K). The heating took about 1–1.5 h. After the temperature reached the set one, the temperature was kept for appropriate reaction time. The stirring rate was 500 rpm. After reaction, the reactor was cooled down by using ice bath and the gases were collected in a gas bag. The reaction mixture was separated into organic and aqueous phases. The autoclave contents were transferred to a vial, and the catalyst was separated by centrifugation and filtration. With prereduced 5 wtpercent Pt-Ir alloy particle covered with ReOx supported on silica in decane, water, Time= 24h, T= 179.84 °C , p= 3750.38Torr , Inert atmosphere, Autoclave Liu, Sibao; Okuyama, Yasuyo; Tamura, Masazumi; Nakagawa, Yoshinao; Imai, Akio; Tomishige, Keiichi; Catalysis Today; vol. 269; (2016); p. 122 - 131 View in Reaxys

HO HO

Rx-ID: 42478274 View in Reaxys 22/804 Yield

Conditions & References 2.2. Activity tests General procedure: Activity tests were performed in a 190-ml stainless steel autoclave with an inserted glass vessel. The catalyst was put into an autoclave together with a spinner and an appropriate amount of water and heated at 473 K with 8 MPa H2 for 1 h for the reduction pretreatment. The stirring rate was 250 rpm. After the pretreatment, the autoclave was cooled down, and hydrogen was removed.Sorbitol (0.5 g, Wako Pure Chemical Industries, Ltd., 98percent) and n-decane (20 ml; Tokyo Chemical Industry Co. Ltd., 99percent) were put into the autoclave. HZSM-5 was also added when necessary. After sealing the reactor, the air content was purged by flushing three times with Ar (1 MPa, 99.99percent; Nippon Peroxide Co., Ltd.). The reactor was pressurized with Ar to 0.5–4.0 MPa at room temperature and then heated to set temperatures (443–473 K). The heating took about 1–1.5 h. After the temperature reached the set one, the temperature was kept for appropriate reaction time. The stirring rate was 500 rpm. After reaction, the reactor was cooled down by using ice bath and the gases were collected in a gas bag. The reaction mixture was separated into organic and aqueous phases. The autoclave contents were transferred to a vial, and the catalyst was separated by centrifugation and filtration. With prereduced 1 wtpercent Pt-Ir alloy particle covered with ReOx supported on silica in decane, water, Time= 24h, T= 179.84 °C , p= 3750.38Torr , Inert atmosphere, Autoclave Liu, Sibao; Okuyama, Yasuyo; Tamura, Masazumi; Nakagawa, Yoshinao; Imai, Akio; Tomishige, Keiichi; Catalysis Today; vol. 269; (2016); p. 122 - 131 View in Reaxys

O O

HO O

O O

Rx-ID: 42504208 View in Reaxys 23/804

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Yield

Conditions & References

83 %

With Cl(1-)*C5H14NO(1+)*3ZnCl2, Time= 0.166667h, T= 120 °C , Microwave irradiation, Green chemistry, FriedelCrafts Acylation, regioselective reaction Tran, Phuong Hoang; Nguyen, Hai Truong; Hansen, Poul Erik; Le, Thach Ngoc; RSC Advances; vol. 6; nb. 43; (2016); p. 37031 - 37038 View in Reaxys O

O OH

OH O

Rx-ID: 44253534 View in Reaxys 24/804 Yield

Conditions & References With hydrogen in 1,4-dioxane, Time= 2h, T= 179.84 °C , p= 60006Torr , Autoclave, Catalytic behavior, Reagent/ catalyst, Temperature, Time, Overall yield = 34 percent Takeda, Yasuyuki; Tamura, Masazumi; Nakagawa, Yoshinao; Okumura, Kazu; Tomishige, Keiichi; Catalysis Science and Technology; vol. 6; nb. 14; (2016); p. 5668 - 5683 View in Reaxys O

O OH

OH O

Rx-ID: 44253535 View in Reaxys 25/804 Yield

Conditions & References

3.1 %, 89 %, 7.6 %, 0.2 %

With hydrogen in 1,4-dioxane, Time= 24h, T= 139.84 °C , p= 60006Torr , Autoclave, Catalytic behavior, Reagent/ catalyst, Time, Overall yield = > 99 percent Takeda, Yasuyuki; Tamura, Masazumi; Nakagawa, Yoshinao; Okumura, Kazu; Tomishige, Keiichi; Catalysis Science and Technology; vol. 6; nb. 14; (2016); p. 5668 - 5683 View in Reaxys O

O HO

OH O

Rx-ID: 44253537 View in Reaxys 26/804 Yield

Conditions & References With hydrogen in 1,4-dioxane, Time= 4h, T= 159.84 °C , p= 60006Torr , Autoclave, Catalytic behavior, Reagent/ catalyst, Temperature, Time, Overall yield = 31 percent Takeda, Yasuyuki; Tamura, Masazumi; Nakagawa, Yoshinao; Okumura, Kazu; Tomishige, Keiichi; Catalysis Science and Technology; vol. 6; nb. 14; (2016); p. 5668 - 5683 View in Reaxys 2

O– O

Na +

N NH 2

O O

O HO

OH O

O– NH 2

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H 2N

Rx-ID: 44625761 View in Reaxys 27/804 Yield

Conditions & References With natrojarosite, dihydrogen peroxide, Time= 10h, T= 20 °C , pH= 7.3, Irradiation, Catalytic behavior, Reagent/ catalyst, pH-value Dong, Yu; Wang, Ziting; Yang, Xin; Zhu, Meiying; Chen, Rufen; Lu, Bin; Liu, Hui; RSC Advances; vol. 6; nb. 105; (2016); p. 102972 - 102978 View in Reaxys

HO O

Rx-ID: 63375 View in Reaxys 28/804 Yield 100 %

Conditions & References With potassium hydroxide, hydrogen, [RhCl(PPh3)2], Ph2PO2CCH=CMe2 in acetone, Time= 17h, T= 22 °C , p= 2280Torr Preston, Sheila A.; Cupertino, Domenico C.; Palma-Ramirez, Pilar; Cole-Hamilton, David J.; Journal of the Chemical Society, Chemical Communications; nb. 12; (1986); p. 977 - 978 View in Reaxys

90 %

With sodium tetrahydroborate, sodium hydroxide in water, T= 20 - 60 °C Rao, Gopal Krishna; Gowda, Narendra B.; Ramakrishna, Ramesha A.; Synthetic Communications; vol. 42; nb. 6; (2012); p. 893 - 904 View in Reaxys

60 %

With sodium hydroxide, hydrogen, nickel in water, hydrogen generated in situ electrochemically on Raney nickel electrode Chiba; Okimoto; Nagai; Takata; Bulletin of the Chemical Society of Japan; vol. 56; nb. 3; (1983); p. 719 - 723 View in Reaxys With sodium amalgam Baeyer; Justus Liebigs Annalen der Chemie; vol. 251; (1889); p. 266 View in Reaxys Bulk; Justus Liebigs Annalen der Chemie; vol. 139; (1866); p. 66 View in Reaxys With hydrogen, nickel, T= 190 °C Sabatier; Mailhe; Annales de Chimie (Cachan, France); vol. <8>16; (1909); p. 107 View in Reaxys With potassium hydroxide, hydrogen, lt;RhCl(PPh3)2(PH2PO2CCH=CMe2)gt; in acetone, Time= 17h, T= 22 °C , p= 2280Torr , Yield given Iraqi, Ahmed; Fairfax, Neil R.; Preston, Sheila A.; Cupertino, Domenico C.; Irvine, Derek J.; Cole-Hamilton, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 8; (1991); p. 1929 - 1936 View in Reaxys

99 %Chromat.

With hydrogen, Time= 0.0166667h, T= 20 °C , p= 750.075Torr , Inert atmosphere, Neat (no solvent) Chang, Fei; Kim, Hakwon; Lee, Byeongno; Park, Sungho; Park, Jaiwook; Tetrahedron Letters; vol. 51; nb. 32; (2010); p. 4250 - 4252 View in Reaxys

98 %Chromat.

With iridium, hydrogen in ethanol, Time= 5h, T= 25 °C

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Mekhaev; Pervova; Kazakov; Bratskaya; Pestov; Russian Journal of Organic Chemistry; vol. 51; nb. 2; (2015); p. 279 - 280; Zh. Org. Khim.; vol. 51; nb. 2; (2015); p. 289 - 290,2 View in Reaxys

E O

HO O

Rx-ID: 197439 View in Reaxys 29/804 Yield

Conditions & References With Pd-BaSO4, ethanol, Hydrogenation Paal; Schiedewitz; Chemische Berichte; vol. 63; (1930); p. 768 View in Reaxys With sodium hydroxide, aluminum nickel, T= 90 °C Bougault; Cattelain; Chabrier; Bulletin de la Societe Chimique de France; vol. <5>5; (1938); p. 1711 View in Reaxys Schwenk et al.; Journal of Organic Chemistry; vol. 9; (1944); p. 175 View in Reaxys With ammonium hydroxide, nickel coated zinc Harlay; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 213; (1941); p. 304 View in Reaxys With sodium hydroxide, D-Galactose, nickel Delepine; Horeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 1607; Bulletin de la Societe Chimique de France; vol. <5>4; (1937); p. 1531 View in Reaxys

100 % Spectr.

With hexacarbonyl molybdenum, phenylsilane in tetrahydrofuran, Time= 6.5h, Heating Keinan, Ehud; Perez, Daniel; Journal of Organic Chemistry; vol. 52; nb. 12; (1987); p. 2576 - 2580 View in Reaxys With hydrogen, [RhCl(1,3,5-triaza-7-phosphaadamantane)3] in water, T= 37 °C , pH 4.70 Joo, Ferenc; Nadasdi, Levente; Benyei, Attila Cs.; Darensbourg, Donald J.; Journal of Organometallic Chemistry; vol. 512; nb. 1-2; (1996); p. 45 - 50 View in Reaxys Hydrogenation Paal; Schiedewitz; Chemische Berichte; vol. 63; (1930); p. 768 View in Reaxys With hydrogen, [RhCl(1,3,5-triaza-7-phosphaadamantane)3] in water, T= 37 °C , effect of substrate and catalyst concentration, partial pressure of hydrogen, excess of phosphine, and pH; various substrates, Rate constant, Mechanism Joo, Ferenc; Nadasdi, Levente; Benyei, Attila Cs.; Darensbourg, Donald J.; Journal of Organometallic Chemistry; vol. 512; nb. 1-2; (1996); p. 45 - 50 View in Reaxys With hydrogen, guanidine hydrochloride, RuCl2((3-diphenylphosphino)benzenesulfonate)2 in water, T= 60 °C , p= 750.075Torr , pH= 3.30, Product distribution, Further Variations: Reagents Katho, Agnes; Benyei, Attila C.; Joo, Ferenc; Sagi, Maria; Advanced Synthesis and Catalysis; vol. 344; nb. 3-4; (2002); p. 278 - 282 View in Reaxys With sodium tetrahydroborate, hydrogen in ethanol, T= 45 °C , p= 760.051Torr , Catalytic behavior, Kinetics

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Kalmykov; Magdalinova; Klyuev; Petroleum Chemistry; vol. 55; nb. 1; (2015); p. 63 - 67; Neftekhimiya; vol. 55; (2015); p. 66 - 71,6 View in Reaxys

HO O

Rx-ID: 6188358 View in Reaxys 30/804 Yield 95%

Conditions & References 13 : EXAMPLE 14 6,7-Dimethoxy-2-(3,4-methylenedioxyphenyl)-1-oxo-1,2,3,4-tetrahydronaphthalene) (IX) EXAMPLE 14 6,7-Dimethoxy-2-(3,4-methylenedioxyphenyl)-1-oxo-1,2,3,4-tetrahydronaphthalene) (IX) A mixture of 22 grams (0.062 mole) of the product of Example 13 and 3 grams of 10percent Pd/C in 200 milliliters of acetic acid in the presence of 1.5 milliliters of 70percent perchloric acid was hydrogenated at 55°-60° C. under 4 kg./cm2 for 2 hours. The catalyst was filtered from the warm reaction mixture and washed with acetic acid (3 * 40 milliliters). The combined filtrate and washings were evaporated to dryness in vacuo. The residue was extracted with benzene (4 * 300 milliliters). The benzene extract was washed with water (3 * 150 milliliters) and dried (sodium sulfate). Evaporation of solvent gave 20 grams (95percent yield) of the butyric acid; λmax (ethanol) 230,280 nm. Patent; The United States of America as represented by the Department of Health, Education and Welfare; US4014885; (1977); (A1) English View in Reaxys

77%

40 : Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-2-[[[(2-methyl-1-cyclohexyl)oxy]carbonyl]amino]-1-oxopropyl]amino]-1-phenylethyl]amino]-4-oxo-[1 R-[1α[R*(R*)]2β]]-((-)-isomer) EXAMPLE 40 Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-2-[[[(2-methyl-1-cyclohexyl)oxy]carbonyl]amino]-1-oxopropyl]amino]-1-phenylethyl]amino]-4-oxo-[1 R-[1α[R*(R*)]2β]]-((-)-isomer) The amine 60K in Scheme IX (100 mg, 0.21 mmol) as a solution in EtOAc (30 mL) was treated with succinic anhydride (30 mg, 0.3 mmol) and left stirring at room temperature for 18 h before the solvent was removed in vacuo and the residue chromatographed over reverse phase silica gel using 60percent MeOH in H2 O as eluant to give the product (93 mg, 77percent); mp 106°-111° C. (MeOH/H2 O); [α]20 D -33.5° (c=0.81, MeOH), IR (film) 3320, 2933, 2860, 1714 and 1661 cm-1; NMR (CDCl3) δ 0.88 (3H, d, J 6.5 Hz), 1.0-1.35 (4H, m), 1.47 (3H, s), 1.40-1.80 (4H, m), 1.95-2.05 (1H, br m), 2.40-2.65 (4H, m), 3.20-3.35 (3H, m), 3.75-3.85 (1H, m), 4.20-4.30 (1H, m), 4.90-5.00 (1H, br s), 5.30-5.40 (1H, br s), 6.40-6.50 (1H, br s), 6.97 (1H, s), 7.05-7.30 (8H, m), 7.33 (1H, d, J 8 Hz), 7.54 (1H, d, J 8 Hz), 8.60 (1H, s); MS(FAB) m/e 577.2 (M+1) and 217.0 (100); Anal. C32 H40 N4 O6. 0.5H2 O; C, H, N. Patent; Warner-Lambert Company; US5278316; (1994); (A1) English View in Reaxys

77%

40 : Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-2-[[[(2-methyl-1-cyclohexyl)oxy]carbonyl]amino]-1-oxopropyl]amino]-1-phenylethyl]amino]-4-oxo-[1R-[1α[R*(R*)]2β]]-((-)-isomer) EXAMPLE 40 Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-2-[[[(2-methyl-1-cyclohexyl)oxy]carbonyl]amino]-1-oxopropyl]amino]-1-phenylethyl]amino]-4-oxo-[1R-[1α[R*(R*)]2β]]-((-)-isomer) The amine 60K in Scheme IX (100 mg, 0.21 mmol) as a solution in EtOAc (30 mL) was treated with succinic anhydride (30 mg, 0.3 mmol) and left stirring at room temperature for 18 h before the solvent was removed in vacuo and the residue chromatographed over reverse phase silica gel using 60percent MeOH in H2 O as eluant to give the product (93 mg, 77percent); mp 106°-111° C. (MeOH/H20); [α]D 20 -33.5° (c=0.81, MeOH), IR (film) 3320, 2933, 2860, 1714 and 1661 cm-1; NMR (CDCl3) δ0.88 (3H, d, J 6.5 Hz), 1.0-1.35 (4H, m), 1.47 (3H, s), 1.40-1.80 (4H, m), 1.95-2.05 (1H, br m), 2.40-2.65 (4H, m), 3.20-3.35 (3H, m), 3.75-3.85 (1H, m), 4.20-4.30 (1H, m), 4.90-5.00 (1H, br s), 5.30-5.40 (1H, br s), 6.40-6.50 (1H, br s), 6.97 (1H, s), 7.05-7.30 (8H, m), 7.33 (1H, d, J 8 Hz), 7.54 (1H, d, J 8 Hz), 8.60 (1H, s); MS(FAB) m/e 577.2 (M+1) and 217.0 (100); Anal. C32 H40 N4 O6.0.5 H2 O; C, H, N. Patent; Warner-Lambert Company; US5631281; (1997); (A1) English View in Reaxys

77%

51.A : Preparation of 1-cyclopropyl-N-hydroxy-4-{[4-(3-{3-[4-(trifluoromethoxy) phenyl]-1,2,4-oxadiazol-5yl}propoxy)phenyl]sulfonyl}piperidine-4-carboxamide Hydrochloride Part A.

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In dry equipment under nitrogen, potassium trimethylsilanolate (35.9 g, 0.28 mol) was dissolved in dimethylsulfoxide (250 mL) and gamma-butyrolactone (16.14 mL, 0.21 mol) was added over 10 min while the reaction temperature rose to 38° C. After stirring at ambient temperature for 40 min, sodium hydride (8.4 g of a 60percent oil dispersion, 0.21 mol) was added portion wise over 20 min and the reaction temperature rose to 43° C. Gas evolution was also observed. After stirring at ambient temperature for 50 min, a solution of ethyl 1-cyclopropyl-4-[(4-fluorophenyl)sulfonyl]-4-piperidinecarboxylate (49.7 g, 0.14 mol) in dimethylsulfoxide (50 mL) was added over 10 min as the reaction temperature rose to 38° C. The reaction was stirred at ambient temperature for 30 min. The slurry was slowly poured into ice water (1.5 L) and then extracted with hexanes (150 mL) 3 times followed by a diethyl ether extraction (300 mL). The aqueous layer was chilled to 5° C. and the pH adjusted to 6 with concentrated hydrochloric acid. The slurry was filtered and the cake washed with 500 mL water two times. The solid was dried in vacuo to give the butyric acid as a white solid (47.5 g, 77percent). LCMS m/z=440 [M+H]+. Patent; Freskos, John N.; Fobian, Y vette M.; Awasthi, Alok K.; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Carroll, Jeffery N.; Chandrakumar, Nizal S.; DeCrescenzo, Gary A.; Desai, Bipin N.; Heron, Marcia I.; Hockerman, Susan L.; Jull, Sara M.; Kassab, Darren J.; Kolodziej, Steve A.; McDonald, Joseph; Mischke, Deborah A.; Mullins, Patrick B.; Norton, Monica B.; Rico, Joseph G.; Talley, John J.; Trivedi, Mahima; Villamil, Clara I.; Wang, Lijuan Jane; US2004/24024; (2004); (A1) English View in Reaxys 62%

6.A : PART A PART A Preparation of Butanoic acid, 4-[[2-hydroxy-3-[(3-methylbutyl) (phenylsulfonyl)amino]-1-(phenylmethyl)propyl]amino]-2,2,3-Trimethyl-4-oxo, phenylmethyl ester, [1S-[1R*(S*), 2S*]]- STR41 A solution of 10.1 g (19.3 mmol) of phenylmethyl[2R-hydroxy-3-[(3-methylbutyl) (phenylsulfonyl)amino]-1S -(phenylmethyl)propyl]carbamate from Example 3 in 40 mL of methanol was hydrogenated over 2 g of 10percent palladium-on-carbon under 50 psig of hydrogen for six hours. After flushing with nitrogen, the catalyst was removed by filtration through celite and the filtrate concentrated to provide 7.41 g (99percent) of 2 (R)-hydroxy-3-[(3-methylbutyl) (phenylsulfonyl, amino]-1(S)-(phenylmethyl)propylamine. To a solution of 2.5 g (10.0 mmol) of benzyl 2,2,3 (R)-trimethylsuccinate and 2.1 g (15.0 mmol) of N-hydroxybenzotriazole in 10 mL of anhydrous N,N-dimethylformamide (DMF) at 0° C., was added 2.1 g (11.0 mmol) of 1-(3-dimethyl aminopropyl)-3-ethylcarbodiimide hydrochloride (EDC). After two hours, a solution of 3.9 g (10.0 mmol) of 2 (R) -hydroxy-3-[(3-methylbutyl) (phenylsulfonyl)amino]-1S-(phenylmethyl)propylamine in 3 mL of DMF was added. After stirring at room temperature for sixteen hours, the solvent was removed under reduced pressure, the residue dissolved in ethyl acetate and then washed with 0.2 N citric acid, 5percent aqueous soduim bicarbonate, saturated brine, dried over anhydrous magnesuim sulfate, filtered and concentrated to afford 5.74 g of crude product. This was chromatographed over silica gel using 1percent methanol/methylene chloride as eluent (Rf =0.08) to afford 3.87 g (62percent yield) of the desired product, m/e=533 (M+H+). Patent; G. D. Searle and Co.; US5463104; (1995); (A1) English View in Reaxys

61.3%

3 : EXAMPLE 3 The product, butanoic acid, 3,3'-[[[[(2-ethoxy-2-oxoethyl]amino]methyl]phosphinylidene]bis-(oxy)]bis-, diethyl ester was obtained as a viscous yellow oil in 61.3percent yield (9.2 g) having the following analysis: Calculated: C, 48.00; H, 7.58; N, 3.29; P, 7.28; Found: C, 47.03; H, 7.48; N, 3.56; P, 8.07. Patent; Monsanto Company; US4388102; (1983); (A1) English View in Reaxys

61.3%

15 : EXAMPLE 15 The product, butanoic acid, 3,3'-[[[[(2-ethoxy-2-oxoethyl]amino]methyl]phospinylidene]bis-(oxy)]bis-, diethyl ester was obtained as a viscous yellow oil in 61.3percent yield (9.2 g) having the following analysis: Calculated: C, 48.00; H, 7.58; N, 3.29; P, 7.28; Found: C, 47.03; H, 7.48; N, 3.56; P, 8.07. Patent; Monsanto Company; US4442044; (1984); (A1) English View in Reaxys

51%

42.A : Preparation of:

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Part A. In dry equipment under nitrogen, potassium trimethylsilanolate (42.76 g, 0.3 mol) was dissolved in dimethylsulfoxide (170 mL) and gamma-butyrolactone (17.31 mL, 0.225 mol) was added over 5 min while the reaction temperature rose to 49 C. After stirring at ambient temperature for 90 min, sodium hydride (9.0 g of a 60percent oil dispersion, 0.225 mol) was added portion wise over 20 min and the reaction temperature rose to 38° C. Gas evolution was also observed. After stirring at ambient temperature for 40 min, a solution of ethyl 4-[(4-fluorophenyl)sulfonyl]-1-(2-methoxyethyl)piperidine-4-carboxylate (56 g, 0.15 mol) in dimethylsulfoxide (20 mL) was added over 10 mins as the reaction rose to 38° C. The reaction was stirred at ambient temperature for 30 min. The slurry was slowly poured into ice water (1.1 L) and then extracted with hexanes (300 mL) two times followed by a diethyl ether extraction (200 mL). The aqueous layer was chilled to 5° C. and the pH adjusted to 7 with concentrated hydrochloric acid. The aqueous solution was extracted with methylene chloride (150 mL) until there was no WV activity in the extract. The combined methylene chloride extracts were washed with saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated in vacuo. The solid was recrystallized from methanol (200 mL) to give the butyric acid as a white solid (34.8 g, 51percent). LCMSm/z=458 [M+H]+. Patent; Freskos, John N.; Fobian, Y vette M.; Awasthi, Alok K.; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Carroll, Jeffery N.; Chandrakumar, Nizal S.; DeCrescenzo, Gary A.; Desai, Bipin N.; Heron, Marcia I.; Hockerman, Susan L.; Jull, Sara M.; Kassab, Darren J.; Kolodziej, Steve A.; McDonald, Joseph; Mischke, Deborah A.; Mullins, Patrick B.; Norton, Monica B.; Rico, Joseph G.; Talley, John J.; Trivedi, Mahima; Villamil, Clara I.; Wang, Lijuan Jane; US2004/24024; (2004); (A1) English View in Reaxys aus Kohlenhydraten und aus mehrwertigen Alkoholen durch Clostridium felsineum Bergey et al. Muratowa; ; vol. 6; (1937); p. 366; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 2917 View in Reaxys durch Vergaerung von Melasse Patent; Comm.Solv.Corp.; US1913346; (1929) View in Reaxys Owen; Chemisches Zentralblatt; (1937); p. II 302 View in Reaxys Osburn,Stritar,Werkman; Chemisches Zentralblatt; (1935); p. II 2750 View in Reaxys Patent; Borinquen Assoc.; US2181310; (1936) View in Reaxys durch Vergaerung von Holzzucker Sjolander; Langlykke; Peterson; Industrial and Engineering Chemistry; vol. 30; (1938); p. 1254 View in Reaxys durch Vergaeren zuckerhaltiger Abfallprodukte Waksman; Kirsh; Industrial and Engineering Chemistry; vol. 25; (1933); p. 1036 View in Reaxys Gewinnung aus Sulfitablauge Daniels; McCarthy; ; vol. 126; nb. 5; (1948); p. 43; ; (1948); p. 2051 View in Reaxys durch Vergaeren von Melasse, Sulfitablauge und anderen staerke- oder zuckerhaltigen Abfallprodukten Rector; ; vol. 2; (1948); p. 694 View in Reaxys Bernhauer; View in Reaxys Lorenz;

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View in Reaxys technische Gewinnung durch Vergaerung von hydrolysierter Cellulose durch Buttersaeure-Bakterien Depasse; ; vol. 43; p. 410; Chem. Zentralbl.; vol. 97; nb. II; (1926); p. 1709 View in Reaxys beim anaeroben Wachstum von Dysenterie-Bakterien in peptonhaltigem zuckerfreiem Naehrboden Zoller; Clark; ; vol. 3; p. 329; Chem. Zentralbl.; vol. 92; nb. I; (1921); p. 775 View in Reaxys Buttersaeuregaerung mit Hilfe der Reinkultur eines bestimmten Buttersaeurebacteriums Buchner; Meisenheimer; Chemische Berichte; vol. 41; (1908); p. 1411 View in Reaxys Fitz; Chemische Berichte; vol. 11; (1878); p. 42; Chemische Berichte; vol. 13; (1880); p. 1309 View in Reaxys Bei der anaeroben Gaerung von Tartraten Ordonneau; Bulletin de la Societe Chimique de France; vol. <4>9; (1911); p. 400 View in Reaxys Zur Bildung durch 'Buttersaeuregaerung' Oppenheimer,C.; View in Reaxys Czapek,F.; View in Reaxys Darstellung aus den Rueckstaenden der Weinbrennerei Thuau; Chem. Zentralbl.; vol. 81; nb. II; (1910); p. 1253 View in Reaxys Horner,L. et al.; Chemische Berichte; vol. 94; (1961); p. 1987 - 1996 View in Reaxys Leete,E.; Journal of the American Chemical Society; vol. 86; (1964); p. 2509 - 2513 View in Reaxys Ferris,A.F.; Journal of Organic Chemistry; vol. 25; (1960); p. 12 - 18 View in Reaxys Nakagawa,K. et al.; Journal of Organic Chemistry; vol. 27; (1962); p. 1597 - 1601 View in Reaxys Bailey,P.S. et al.; Journal of Organic Chemistry; vol. 33; (1968); p. 2675 - 2680 View in Reaxys Rasmussen,J.K.; Hassner,A.; Journal of Organic Chemistry; vol. 38; (1973); p. 2114 - 2115 View in Reaxys Lee,J.B.; Clarke,T.G.; Tetrahedron Letters; (1967); p. 415 - 422 View in Reaxys Ayyangar et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 16; (1978); p. 555 View in Reaxys Clarke et al.; Journal of the Chemical Society [Section] C: Organic; (1970); p. 815 View in Reaxys Broadbent; Selin; Journal of Organic Chemistry; vol. 28; (1963); p. 2343 View in Reaxys Dittmer et al.; Chemistry and Industry (London, United Kingdom); (1964); p. 152 View in Reaxys Vereshchagin et al.; Zhurnal Organicheskoi Khimii; vol. 11; (1975); p. 292,285 View in Reaxys Freidlina et al.; Doklady Chemistry; vol. 156; (1964); p. 623; Doklady Akademii Nauk SSSR; vol. 156; (1964); p. 1133 View in Reaxys Koelbel et al.; Justus Liebigs Annalen der Chemie; vol. 632; (1960); p. 8,13

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View in Reaxys Heyns; Blazejewicz; Tetrahedron; vol. 9; (1960); p. 67,73 View in Reaxys Suga et al.; Bulletin of the Chemical Society of Japan; vol. 38; (1965); p. 893,895 View in Reaxys Ohno et al.; Agricultural and Biological Chemistry; vol. 26; (1962); p. 460 View in Reaxys Tanaka; Nippon Kagaku Kaishi; vol. 80; (1959); p. 545; ; vol. 55; nb. 3419; (1961) View in Reaxys Nakagawa et al.; Chemical and Pharmaceutical Bulletin; vol. 12; (1964); p. 403,405 View in Reaxys Grekov et al.; Zhurnal Organicheskoi Khimii; vol. 6; (1970); p. 94,93 View in Reaxys Ogibin et al.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 23; (1974); p. 2156; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 23; (1974); p. 2239 View in Reaxys Markman; Sinkowa; J. Gen. Chem. USSR (Engl. Transl.); vol. 32; (1962); p. 353,346; ; vol. 58; nb. 6664; (1963) View in Reaxys Bestmann; Schulz; Chemische Berichte; vol. 95; (1962); p. 2921,2926 View in Reaxys Wang; Ikeda; Biochemical Journal; vol. 79; (1961); p. 614,615-620; ; nb. 26100; (1961) View in Reaxys Smeykal et al.; Journal fuer Praktische Chemie (Leipzig); vol. 30; (1965); p. 126,128; ; nb. q View in Reaxys Shostenko et al.; High Energy Chemistry; vol. 10; (1976); p. 330 View in Reaxys Patent; Karl Ziegler; FR1330718; (1960); ; vol. 60; nb. 545g; (1964) View in Reaxys Kaulen; Schaefer; Synthesis; (1979); p. 513 View in Reaxys Deno; Greigger; Messer; et al.; Tetrahedron Letters; vol. No. 20; (1977); p. 1703 - 1704 View in Reaxys Broi-Karre; Proskuryakov; J. Appl. Chem. USSR (Engl. Transl.); vol. 38; (1965); p. 2779,2708,2709 View in Reaxys Matsui et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 562,565 View in Reaxys Schrumpf; Klein; Chemische Berichte; vol. 106; (1973); p. 266,278 View in Reaxys Oehlmann; Schirmer; Kinetics and Catalysis; vol. 8; (1967); p. 629 View in Reaxys Suhara; Yukagaku; vol. 25; (1976); p. 75,77; ; vol. 85; nb. 32375x View in Reaxys Sooma; Sano; Kogyo Kagaku Zasshi; vol. 73; (1970); p. 2723; ; vol. 74; nb. 111515; (1971) View in Reaxys Francke; Bruemmer; Planta Medica; vol. 34; (1978); p. 332,333 View in Reaxys Vikhorev et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 48; (1975); p. 2698,2779,2781 View in Reaxys Lee; Chang; Journal of Organic Chemistry; vol. 44; (1979); p. 2726,2728 View in Reaxys Keinan; Mazur; Journal of Organic Chemistry; vol. 42; (1977); p. 844,845 View in Reaxys Syroezhko et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 48; (1975); p. 1889,1962 View in Reaxys Vikhorev et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 48; (1975); p. 2076,2144 View in Reaxys Freidlina et al.; Mendeleev Chemistry Journal; vol. 11; (1966); p. 156,159; ; p. 211 View in Reaxys Komshilov et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 38; (1965); p. 650,649 View in Reaxys Taniguchi et al.; Bulletin of the Chemical Society of Japan; vol. 45; (1972); p. 3380,3381,3382

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View in Reaxys Komshilov et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 38; (1965); p. 1337,1313 View in Reaxys Babel; Proskuryakov; J. Appl. Chem. USSR (Engl. Transl.); vol. 38; (1965); p. 1085,1064,1067 View in Reaxys Schroeder; Griffith; Journal of the Chemical Society, Chemical Communications; (1979); p. 58 View in Reaxys Manakow et al.; Neftekhimiya; vol. 10; (1970); p. 860; ; vol. 74; nb. 63870; (1971) View in Reaxys Potekhin; Proskuryakov; J. Appl. Chem. USSR (Engl. Transl.); vol. 38; (1965); p. 462,472 View in Reaxys Kirillow et al.; Journal of Organic Chemistry USSR (English Translation); vol. 2; (1966); p. 1040; Zhurnal Organicheskoi Khimii; vol. 2; (1966); p. 1048 View in Reaxys Takita et al.; Bulletin of the Chemical Society of Japan; vol. 51; (1978); p. 669 View in Reaxys Chiang; Li; Huaxue Xuebao; vol. 28; (1962); p. 379; ; vol. 59; nb. 12636; (1963) View in Reaxys Oae et al.; Journal of Labelled Compounds; vol. 4; (1968); p. 28,29-40 View in Reaxys Clarke et al.; Tetrahedron Letters; (1968); p. 5685 View in Reaxys Story et al.; Tetrahedron Letters; (1968); p. 3291 View in Reaxys Simmons; Kreuz; Journal of Organic Chemistry; vol. 33; (1968); p. 836 View in Reaxys Bachman; Strawn; Journal of Organic Chemistry; vol. 33; (1968); p. 313 View in Reaxys When tested as described above, compounds of the present invention, including: 2-amino-4-[1-(carboxymethyl-carbamoyl)-2-(2-hexyloxycarbonyl-2-oxo-ethylsulfanyl)-ethylcarbamoyl]-butyric acid, 2-amino-4-[1-(carboxymethyl-carbamoyl)-2-(2-carboxy-2-oxo-ethylsulfanyl)-ethylcarbamoyl]butyric acid, 2-amino-4-[1-(carboxymethyl-carbamoyl)-2-(2-ethoxycarbonyl-2-oxo-ethylsulfanyl)-ethylcarbamoyl] butyric acid, Patent; Wang, Bing; Miller, Guy; Flaim, Stephen F.; Del Balzo, Ughetta; Zhang, Wei; Janagani, Satyanarayana; Song, Jiangao; US2003/13656; (2003); (A1) English View in Reaxys 79.A : Example 79 Part A. Preparation of Butanoic Acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-, Methyl Ester, (3S)N-t-BOC-L-Aspartic Acid Beta-Methyl Ester (Sigma) (2.00 g, 8.09 mmol, 1 equiv.) was dissolved in 25 ml of THF at 25° C. under N2. 1.0M Borane in THF (24.27 ml, 24.3 mmol, 3 equiv.) was added dropwise at 0° C. over 10 minutes. The reaction was stirred 1 hour at 0° C. and then carefully quenched with the dropwise addition of MeOH followed by 2 ml of acetic acid. The mixture was stripped to obtain an oil which was treated with 10 ml of H2O followed by adjusting the pH to 8-9 with NaHCO3 then extracted 3 times with EtOAc. The organic layers were combined, dried and stripped to give a colorless oil which was purified over silica gel in 3:1 hexanes/EtOAc to 100percent EtOAc. Patent; Duncia, John V.; Santella, Joseph B.; Wacker, Dean A.; Yao, Wenqing; Zheng, Changsheng; US2002/156102; (2002); (A1) English View in Reaxys 79.C : Example 79 Part C. Preparation of Butanoic Acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-iodo-, Methyl Ester, (3S)Butanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[(methylsulfonyl)oxy]-methyl ester, (3S)-(0.46 g, 1.48 mmol, 1 equiv.) was dissolved in 10 ml of acetone at 25° C. under N2 and NaI (1.11 g, 7.39 mmol, 5 equiv.) was added thereto. The mixture was refluxed for 1 hour.

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The solids were filtered and the filtrate was stripped to obtain an oil which was purified over silica gel in (3:1 hexanes/EtOAc). Obtained 164 mg of an amber oil as product NMR (300 MHz, CDCl3) δ 5.20-5.00 (m, 1H), 4.00-3.80 (m, 1H), 3.70 (s, 3H), 3.50-3.30 (m, 2H), 2.80-2.60 (m, 2H), 1.43 (s, 9H). Patent; Duncia, John V.; Santella, Joseph B.; Wacker, Dean A.; Yao, Wenqing; Zheng, Changsheng; US2002/156102; (2002); (A1) English View in Reaxys Within the definitions given, acyl groups can be aromatic, aliphatic, mixed aromatic-aliphatic, cycloaliphatic or bicycloaliphatic or unsaturated, for example derived from the following acids: ... stearic acid, polyisobutenylsuccinic acid, n-hexacosanoic acid, trimethylacetic acid, butyric acid, isovaleric acid, lauric acid, oleic acid, ... Patent; Ciba Specialty Chemicals Corporation; US6140326; (2000); (A1) English View in Reaxys Synthesis and use of 4-(4-N-maleimidophenyl)butyric acid hydrazide (MPBH) 4-(4-N-Maleimidophenyl)butyric acid, N-2-t-butyloxycarbonylhydrazide (1.50 g, 4.02 mmol) was dissolved in 4N HCl in dioxane (10 ml) and stirred at room temperature (30 min). Excess HCl was removed by degassing with argon, and the solvent by evaporation. The residue was triturated with ether (3*) and dried under vacuum to give 4-(4-N-maleimidophenyl)butyric acid, hydrazide, hydrochloride (1.02 g, 82percent), as a pale yellow powder. 1 H NMR (d6 -DMSO) d 10.4 (br s, 2H, NH2), 7.31 (d, J=8.3 Hz, 2H, Ar), 7.25 (d, J=8.3 Hz, 2H, Ar), 7.18 (s, 2H, CH=CH), 3.45 (br s, 2H, NH2), 2.64 (t, J=7.5 Hz, 2H, CH2 Ph), 2.27 (t, J=7.3 Hz, 2H, CH2 CO), 1.87 (m, 2H, CH2); IR (KBr) 2940, 1708, 1516 (s), 1401, 1151, 823 (s), 690 (s) cm-1; MS (FAB) m/e (rel abundance) 274 (MH+, 100). Anal. found: C, 54.1; H, 5.1; N, 13.3percent. C14 H15 N3 O3.HCl requires C, 54.3; H, 5.2; N, 13.6percent. Patent; Genentech, Inc.; US5329028; (1994); (A1) English View in Reaxys 14 : Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3.3.1.13,7 ]dec-2-yloxy)carbonyl]-amino[-1-phenylethyl]amino]-4-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, [R-(R*,R*)]- STR35 EXAMPLE 14 Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3.3.1.13,7 ]dec-2-yloxy)carbonyl]-amino[-1-phenylethyl]amino]-4-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, [R-(R*,R*)]- STR35 To a solution of the above acid (500 mg) in DMF (5 mL) was added NEt3 (117 mg) followed by CCCH2 O2 CCMe3 (247 mg). the reaction mixture was stirred for 5 days at room temperature and then poured into H2 O. the product was extracted with EtOAc and the organic layer dried (MgSO4) and concentrated to yield a gum (750 mg). The crude product was purified by column chromatography (50percent to 75percent EtOAc/hexane) to yield the desired dilute ester (2) as an amorphous white solid (120 mg), mp 110°-115° C.; IR (film) 3317, 3061, 1757, 1700, 1666 cm-1; 1 H-NMR (d6 -DMSO) δ1.12 (12H, brs), 1.49 (2H, brs) 1.60-2.05 (12H, m), 2.50 (4H, m, observed by DMSO), 3.20-3.40 (4H, m, observed by H2 O), 4.69 (1H, brs), 4.96 (1H, m), 5.65 (2H, s), 6.72 (1H, brs), 6.93 (2H, brs), 7.01 (1H, t, J 8 Hz), 7.30 (6H, m), 7.43 (1H, d, J 8 Hz), 7.74 (1H, t, J 4 Hz), 8.16 (1H, brs), 10.86 (1H, s). Patent; Warner-Lambert Company; US5340825; (1994); (A1) English View in Reaxys 9.3 : Step 3 Step 3

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A solution of the amine from Step 2 (Scheme V, No. 6) (0.2 g, 0.37 mmol) in EtOAc (15 mL) was treated with succinic anhydride (0.044 g, 0.44 mmol) and stirred at reflux with N,N-dimethyl amino pyridine (0.061 g, 0.50 mmol) for 18 hours. This mixture was then evaporated to dryness and the residue chromatographed over reverse phase silica using 5:1; MeOH:H2 O as eluent to give the product (Example 1) as a white solid (0.157 g, 66percent), m.p. 137°-150° C.; [α]D 20

=+32° (c=0.5, MeOH); IR (film) 3500-3200, 2910, 2856, 1712, 1651, and 1531 cm-1; NMR (DMSO-d6 +D20 δ1.23

(1.5H, s), 1.29 (1.5H, s), 1.35-1.55 (2H, m), 1.60-2.00 (14H, m), 2.20-2.55 (4H, m), 2.70-2.85 (2H, m), 3.10-3.60 (2H, m), 3.85-4.00 (1H, m), 4.60-4.70 (1H, m), 5.00-5.10 (1H, M), 6.60-6.70 (1H, m), 6.85-7.25 (7H, m), 7.31 (1H, d, J 8 Hz), 7.46 (1H, d, J 8 Hz), 7.30-7.55 (1H, m), 8.23 (1H, d, J 9 Hz); Analysis for C37 H44 N4 O6: Calcd: C, 67.92; H, 7.00; N, 8.56. Found: C, 67.96; H, 6.87; N, 8.65. Patent; Warner-Lambert Company; US5397788; (1995); (A1) English View in Reaxys Examples of monobasic carboxylic acids include: aliphatic monobasic carboxylic acids such as acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, heptanoic acid, caprylic acid, 2,2-dimethylpropionic acid, 3-methylbutyric acid, 3,3-dimethylbutyric acid, ... Patent; Mitsui Toatsu Chemicals, Inc.; US5359117; (1994); (A1) English View in Reaxys 610 mg (59%)

39.B : EXAMPLE 39 Part B. To a solution of 440 mg (1.98 mmol) of the product from part A and 437 mg (2.86 mmol) of HOBT in 9 mL of DMF at 0° C. was added 427 mg (2.23 mmol) of EDC. After 30 minutes at 0° C., a solution of 653 mg (1.87 mmol) of the product from Example 34, Part E, in 3 mL DMF was added. After 1 hour at 0° C. and 15 hours at RT, ethyl acetate was added, extracted with sat'd NaHCO3, 5 percent aqueous citric acid, dried and concentrated to afford 0.98 g of crude product. Chromatography on silica gel using 0-10percent ethyl acetate afforded 610 mg (59percent) of pure butanoic acid, 4[[3-[[[(1,1-dimethylethyl)-amino]carbonyl](3-methylbutyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]amino]-3-methyl-4oxo, [1S-[1R*(3R*), 2S*], benzyl ester. Patent; Monsanto Company; US5475013; (1995); (A1) English View in Reaxys 79 : Butanoic acid, 4-[[2-[[4-(1H-indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3-3.1.13,7 ]dec-2-yloxy)carbonyl]amino]butyl]amino]-1-phenylethyl]amino]-4- oxo-(indole center is RS, other center is R) (R1 =2-adamantyl R3 =H, R4 =NHCOCH2 CH2 CO2 H, c=1, C* =R)) Butanoic acid, 4-[[2-[[4-(1H-indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3-3.1.13,7 ]dec-2-yloxy)carbonyl]amino]butyl]amino]-1-phenylethyl]amino]-4- oxo-(indole center is RS, other center is R) m.p. 115°-125° C., CI-MS (C4 H10):m/z 629 (MH+, 1), 191 (28), m3 5 (100) Patent; Warner-Lambert Company; US5593967; (1997); (A1) English View in Reaxys II. Compounds containing acid groups, such as, carboxylic acids acetic acid propionic acid butyric acid valeric acid caproic acid caprylic acid capric acid

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lauric acid myristic acid palmitic acid ... Patent; Schering Aktiengesellschaft; US5501863; (1996); (A1) English View in Reaxys The process of claim 14 wherein the neutralizing acid is selected from any one of the following: HCl NNO3 H2 SO4 butyric acid. Patent; NanoSystems L.L.C.; US5662883; (1997); (A1) English View in Reaxys The process of claim 36 wherein the neutralizing acid is selected from any one of the following: HCl NNO3 H2 SO4 butyric acid. Patent; NanoSystems L.L.C.; US5662883; (1997); (A1) English View in Reaxys 5 : EXAMPLE 5 EXAMPLE 5 The reactor of Example 1 was charged with a mixture of 0.50 g Ru3 (CO)12, 1.0 g I2, and 50 ml. of acetic acid. Equimolar amounts of CO and H2 were then added to attain a pressure of 3000 psi at 25°. The contents were heated to 250° and shaken for two hours. Analysis by gas chromatography showed that 9.55 g of propionic acid and 1.59 g of butyric acid had been produced. Patent; Union Carbide Chemicals and Plastics Company Inc.; US4897473; (1990); (A1) English View in Reaxys 15 : EXAMPLE 15 In a similar way and starting from (Z)-4-/(2-methoxy-phenoxy)-methyl/-2-bromo-methyl (1,3)-dioxolane and from a (1:1) mixture of the Z and E isomers, the following compounds are obtained respectively: 3-oxa-4-/4-(2-methoxyphenoxy)methyl-(Z)-(1,3) dioxolan-2-yl/butanoic acid, m.p. 64°-66° C. and 3-oxa-4-/(2-methoxyphenoxy)methyl-(Z,E)-(1,3)-dioxolan-2-yl/butanoic acid, m.p. 68°-69° C. Patent; Boehringer Mannhein Italia, S.p.A.; US4968706; (1990); (A1) English View in Reaxys 15 : EXAMPLE 15 A suspension of this compound in aqueous NaOH N (20 ml) is stirred for 3 hours at room temperature to obtain a clear solution which is then extracted with ethyl acetate (2*10 ml) and the organic phase is discarded. The aqueous phase is acidified to pH 2.5-3 by treatment with a 10percent aqueous KHSO4 solution and extracted with ethyl acetate (5*10 ml). These organic extracts are collected, washed with water (2*10 ml) dried on Na2 SO4 and concentrated to dryness under vacuum. The residue crystallizes from diisopropyl ether affording 2.0 g of 3-oxa-4-/4-(2-methoxy-phenoxy)methyl-(E) (1,3)-dioxolane-2-yl/butanoic acid; m.p.86°-88° C. Patent; Boehringer Mannhein Italia, S.p.A.; US4968706; (1990); (A1) English View in Reaxys 6 : EXAMPLE 6 EXAMPLE 6 The procedure of Example 5 was followed exactly except that 0.60 g of I2 was used instead of 1.0 g. Analysis by gas chromatography showed that 5.47 g of propionic acid and 1.00 g of butyric acid had been produced. Patent; Union Carbide Chemicals and Plastics Company Inc.; US4897473; (1990); (A1) English

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View in Reaxys D.1 : Butanoic acid, 2-(1-amino-2,2,2-trifluoro-ethylidene)-3-oxo-4-(4'-chlorophenoxyl)-, ethyl ester. Butanoic acid, 2-(1-amino-2,2,2-trifluoro-ethylidene)-3-oxo-4-(4'-chlorophenoxyl)-, ethyl ester. Through a magnetically stirred solution of 25.67 g (0.1 mol) of product of Example D1 and 0.34 g (0.003 mol) of potassium t-butoxide in 200 mL of dry THF was passed CF3 CN at 25° C. After 9.8 g (0.103 mol) of CF3 CN had been added, the reaction was complete. Solvent was evaporated in vacuo and the residue was recrystallized from hot Et2 O (200 mL) affording 20.39 g (58percent) of product as a light beige solid: mp 108°-110° C. Patent; Monsanto Company; US4936905; (1990); (A1) English View in Reaxys 43 : 1-BUTANOIC ACID, 4,4'-{(TRIDECYLIDENE)BIS(OXY)}BIS-METHYL CARBOXYLATE EXAMPLE 43 1-BUTANOIC ACID, 4,4'-{(TRIDECYLIDENE)BIS(OXY)}BIS-METHYL CARBOXYLATE The diol (1 g; from example 40) was oxidized with pyridinium dichromate (7.33 g) in dry DMF (14 ml) as in example 4A to provide crude diacid which was treated with diazomethane as in example 4B. Chromatography of the crude dimethylester on TLC grade silica gel (30 g) using 5percent acetone in n-Hexane as eluent provided the pure dimethylester (0.28 g) as a yellow oil. Patent; Schering Corporation; US4696946; (1987); (A1) English View in Reaxys 20 : BUTANOIC ACID, 4,4'-[PENTADECYLIDENEBIS(OXY)]BISEXAMPLE 20 BUTANOIC ACID, 4,4'-[PENTADECYLIDENEBIS(OXY)]BIS0.65 g of the product from example 19 was hydrolyzed in 12 ml of absolute EtOH and 8.1 ml of 10percent aqueous KOH as in example 13 to provide the pure diacid. Patent; Schering Corporation; US4758594; (1988); (A1) English View in Reaxys 4.B : BUTANOIC ACID, 4,4'-[2-PENTADECYNYLIDENEBIS(OXY)]BIS-, DIMETHYL ESTER B. The two reactions from above were combined and treated with diazomethane (from 6.5 g diazald). Excess diazomethane was removed by carefully bubbling nitrogen through the solution. Evaporation of diethylether gave the crude diester which was chromatographed on TLC grade silica gel (50 g) using 5percent acetone in n-Hexane as eluent. The pure dimethylester (0.6813 g) was obtained as a yellowish oil. Patent; Schering Corporation; US4758594; (1988); (A1) English View in Reaxys 43 : 1-BUTANOIC ACID, 4,4'-[(TRIDECYLIDENE)BIS(OXY)]BIS-DIMETHYL ESTER EXAMPLE 43 1-BUTANOIC ACID, 4,4'-[(TRIDECYLIDENE)BIS(OXY)]BIS-DIMETHYL ESTER The diol (1 g; from example 42) was oxidized with pyridinium dichromate (7.33 g) in dry DMF (14 ml) as in example 4A to provide crude diacid which was treated with diazomethane as in example 4B. Chromatography of the crude dimethylester on TLC grade silica gel (30 g) using 5percent acetone in n-Hexane as eluent provided the pure dimethylester (0.28 g) as a yellow oil. Patent; Schering Corporation; US4758594; (1988); (A1) English View in Reaxys 44 : 1-BUTANOIC ACID, 4,4'-[(TRIDECYLIDENE)BIS(OXY)]BIS EXAMPLE 44 1-BUTANOIC ACID, 4,4'-[(TRIDECYLIDENE)BIS(OXY)]BIS A solution of the dimethylester (0.2 g; from example 43) in ethanol was treated with 10percent aqueous NaOH (2 ml) and the mixture refluxed for 4 hours. Work-up of the reaction as in example 5 yielded the pure diacid (0.15 g) as a crystalline solid, m.p. 33° C. Patent; Schering Corporation; US4758594; (1988); (A1) English View in Reaxys

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44 : 1-BUTANOIC ACID, 4,4'-{(TRIDECYLIDENE)BIS(OXY)}BIS EXAMPLE 44 1-BUTANOIC ACID, 4,4'-{(TRIDECYLIDENE)BIS(OXY)}BIS A solution of the dimethylester (0.2 g; from (example 41) in ethanol was treated with 10percent aqueous NaOH (2 ml) and the mixture refluxed for 4 hours. Work-up of the reaction as in example 5 yielded the pure diacid (0.15 g) as a crystalline solid, m.p. 33° C. Patent; Schering Corporation; US4696946; (1987); (A1) English View in Reaxys 4 : EXAMPLE 4 EXAMPLE 4 Carbon dioxide 90 mole percent/dimethyl ether 10 mole percent at 2000+-200 psig (137+-13.6 Atm, 13790*103 +-1379*103 Pag) and 52°+-2° C. was used to extract butyric acid from 15 ml of aqueous 0.5 M sodium butyrate. Patent; E. I. Du Pont de Nemours and Company; US4250331; (1981); (A1) English View in Reaxys 5 : BUTANOIC ACID, 4,4'-[2-PENTADECYNYLIDENEBIS(OXY)]BISEXAMPLE 5 BUTANOIC ACID, 4,4'-[2-PENTADECYNYLIDENEBIS(OXY)]BISThe dimethylester (0.5 g; from Example 4) was dissolved in ethanol (10 ml) and treated with 10percent aqueous NaOH (5 ml). After stirring at room temperature for 36 hours, ethanol was evaporated in vacuo, the residue taken up in water and extracted once with diethylether. The remaining aqueous phase was acidified to pH 1.5 with aqueous oxalic acid and extracted with CH2 Cl2. Drying CH2 Cl2 extract over Na2 SO4 followed by evaporation in vacuo provided the pure diacid as a colorless crystalline solid, m.p. 62°-63° C. Yield: 0.4496 g. Patent; Schering Corporation; US4758594; (1988); (A1) English View in Reaxys 5 : EXAMPLE 5 EXAMPLE 5 Monochlorotrifluoromethane 10 mole percent/carbon dioxide 90 mole percent at 2100+-200 psig (143+-13.6 Atm, 14479*103 +-1379*103 Pag) and 52°+-2° C. was used to extract butyric acid from 15 ml of aqueous 0.5 M sodium butyrate. Patent; E. I. Du Pont de Nemours and Company; US4250331; (1981); (A1) English View in Reaxys 8.A : BUTANOIC ACID, 4,4'-[2-NONYNYLIDENEBIS(OXY)]BISA. The product from Example 7 (0.5 g) was oxidized with pyridinium dichromate (4.1 g) in 13 ml of dry DMF at room temperature for 2 days. The mixture was diluted with water (350 ml), and extracted with diethylether (3*100 ml), washed with water, dried (Na2 SO4) and filtered. The solvent was evaporated to give 0.4 g crude diacid which was methylated with diazomethane followed by chromatography to give pure dimethylester which was hydrolyzed as in Example 5 to give 0.3 g pure diacid. Patent; Schering Corporation; US4758594; (1988); (A1) English View in Reaxys 7.13 : (13) The crude product (1.02 g) was dissolved in saturated NaHCO3 aqueous solution. To this NaHCO3 aqueous solution (26 ml) was added 782 mg (5.18 mmols) of methoxycarbonylmaleimide at 0° C. The mixture was stirred at 0° C. for 10 minutes, then diluted with 50 ml of water, stirred at 30° C. for 1 hour and thereafter cooled to 0° C. With addition of several drops of acetic acid, the dilution was stirred at 0° C. for 1 hour. The insolubles were filtered off, and the filtrate was concentrated to obtain a yellow oil. The oil was subjected to TLC (70:30:0.5 ethyl acetate-chloroformacetic acid), giving 367 mg of 4-(2-maleimidophenyl)butyric acid in the form of an oil.

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Patent; Otsuka Pharmaceutical Co.; US4536391; (1985); (A1) English View in Reaxys 1 : Butanoic acid, 3-methyl-2-(((1-(3-(trifluoromethyl)phenyl)ethylidene)amino)oxy-, ethyl ester EMBODIMENT 1 Butanoic acid, 3-methyl-2-(((1-(3-(trifluoromethyl)phenyl)ethylidene)amino)oxy-, ethyl ester In a 500 ml round bottom flask fitted with a magnetic stirrer, Dean-Stark trap and nitrogen purge were placed 2.0 g sodium hydroxide in 15 ml of water. To this was added 10.16 g of 3-(trifluoromethyl)acetophenone oxime in 15 ml of toluene and a catalytic amount of tetrabutylammonium hydrogen sulfate and the mixture was heated to reflux overnight. After cooling, 9.75 g of ethyl 2-bromo-3-methyl butyrate was added all at once and the mixture was refluxed for three days. After cooling, the reaction mixture was filtered and the product was distilled in a Kugelrohr appartus to yield 7.33 g of the desired product; b.p. 90° C. (0.05 mm). Patent; Shell Oil Company; US4537780; (1985); (A1) English View in Reaxys 1 : Process for production of 2-(8-pyrrolizidine)propionic acid To the solution, ether is added and the mixture is allowed to stand, whereby 10.73 g of slightly hygroscopic crystals are obtained. Similarly, 2-(8-pyrrolizidine)butyric acid can be obtained in a yield of 7.54 g. Elemental analysis (percent): C11 H19 NO2: Calcd.: C 66.97, H 9.71, N 7.10. Found: C 67,03, H 9.85, N 7.16. Patent; Suntory Limited; US4831049; (1989); (A1) English View in Reaxys 3 : Butanoic acid, 3-methyl-2-(((1-(3-trifluoromethyl)phenyl)ethylidene)amino)oxy)-, cyano(3-phenoxyphenyl)methyl ester EMBODIMENT 3 Butanoic acid, 3-methyl-2-(((1-(3-trifluoromethyl)phenyl)ethylidene)amino)oxy)-, cyano(3-phenoxyphenyl)methyl ester In a 300 ml round bottom flask equipped with a magnetic stirring bar, reflux condenser and nitrogen purge were placed 40 ml of acetonitrile, 1.52 g of the above carboxylic acid, 0.69 g of powdered potassium carbonate and a catalytic amount of dibenzo-18-crown-6. This mixture was stirred at room temperature for 15 minutes and then 1.38 g alpha-bromo-3-phenoxybenzeneacetonitrile was added and the reaction mixture was stirred at room temperature overnight. The acetonitrile was evaporated and the residue was taken up into methylene chloride for washing with 10percent sodium hydroxide and then drying over magnesium sulfate. The solvent was removed and 1.84 g of the desired product was obtained as a viscous oil. Patent; Shell Oil Company; US4537780; (1985); (A1) English View in Reaxys In addition, a small amount of other organic carboxylic acids, such as indicated below, is formed; for example: Glutaric acid 5-Hydroxycaproic acid 4-Hydroxyvaleric acid Butyric acid Valeric acid Caproic acid Cyclohexylhydroxycaproic acid. Patent; Teijin Limited; US3991099; (1976); (A1) English View in Reaxys 3.a : Example 3 a) a mixture consisting of water (20 g) added with 0.8percent of ascorbic acid, sodium taurocholate (6.0 g), butyric acid (1.5) is prepared; Patent; CHIESI FARMACEUTICI S.p.A.; EP1270007; (2003); (A2) English View in Reaxys 15 : EXAMPLE 15

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In a similar way and starting from (Z)-4-/(2-methoxy-phenoxy)-methyl/-2-bromo-methyl (1,3)-dioxolane and from a (1:1) mixture of the Z and E isomers, the following compounds are obtained respectively; - 3-oxa-4-/4-(2-methoxyphenoxy)methyl-(Z)-(1,3) dioxolan-2-yl/butanoic acid, m.p. 64-66°C and 3-oxa-4-/(2-methoxyphenoxy)methyl-(Z,E)-(1,3)-dioxolan2-yl/butanoic acid, m.p. 68-69°C. Patent; BOEHRINGER MANNHEIM ITALIA S.P.A.; EP303227; (1989); (A1) English View in Reaxys 42 : Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-2-[[[(2-methyl-1-cyclohexyl)oxy]carbonyl]amino]-1-oxopropyl]amino]-3-phenylpropyl]amino]-4-oxo-[1R -[1α[R*(S*)],2β]]-((-)-isomer) EXAMPLE 42 Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-2-[[[(2-methyl-1-cyclohexyl)oxy]carbonyl]amino]-1-oxopropyl]amino]-3-phenylpropyl]amino]-4-oxo-[1R -[1α[R*(S*)],2β]]-((-)-isomer) Methods were employed exactly as for Example 19 except using trans (-)-2-methyl cyclohexyloxycarbonyl-α-methylR-tryptophan (2K in Scheme I) (216 mg, 61percent); mp 97°-102° C. (MeOH/H2 O); [α]D 20 +37° (c=0.22, MeOH); IR (film) 3315, 2930, 2859, 1700 and 1660 cm-1; NMR (CDCl3) δ0.82 (3H, d, J 6.5 Hz), 1.00-1.75 (11H, m), 1.90-2.00 (1H, br s), 2.40-2.70 (6H, m), 2.85-3.00 (1H, br m), 3.23 (1H, d, J 14.5 Hz), 3.30 (1H, d, J 4.5 Hz), 3.45-3.65 (1H, br s), 4.20-4.30 (2H, br m), 5.26 (1H, s), 5.10-5.80 (1H, br), 6.15-6.25 (1H, br s), 6.90-7.20 (9H, m), 7.33 (1H, d, J 8 Hz), 7.53 (1H, d, J 8 Hz), 8.72 (1H, s); MS (FAB) m/e 591.2 (M+1, 100); Anal. C33 H42 N4 O6; C, H, N. Patent; Warner-Lambert Company; US5631281; (1997); (A1) English View in Reaxys 42 : Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-2-[[[(2-methyl-1-cyclohexyl)oxy]carbonyl]amino]-1-oxopropyl]amino]-3-phenylpropyl]amino]-4-oxo-[1R-[1α[R*(S*)],2β]]-((-)-isomer) EXAMPLE 42 Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-2-[[[(2-methyl-1-cyclohexyl)oxy]carbonyl]amino]-1-oxopropyl]amino]-3-phenylpropyl]amino]-4-oxo-[1R-[1α[R*(S*)],2β]]-((-)-isomer) Methods were employed exactly as for Example 19 except using trans-(-)-2-methylcyclohexyloxycarbonyl-α-methylR-tryptophan (2K in Scheme I) (216 mg, 61percent); mp 97°-102° C. (MeOH/H2 O); [α]20 D +37° (c=0.22, MeOH); IR (film) 3315, 2930, 2859, 1700 and 1660 cm-1; NMR (CDCl3) δ 0.82 (3H, d, J 6.5 Hz), 1.00-1.75 (11H, m), 1.90-2.00 (1H, br s), 2.40-2.70 (6H, m), 2.85-3.00 (1H, br m), 3.23 (1H, d, J 14.5 Hz), 3.30 (1H, d, J 14.5 Hz), 3.45-3.65 (1H, br s), 4.20-4.30 (2H, br m), 5.26 (1H, s), 5.10-5.80 (1H, br), 6.15-6.25 (1H, br s), 6.90-7.20 (9H, m), 7.33 (1H, d, J 8 Hz), 7.53 (1H, d, J 8 Hz), 8.72 (1H, s); MS (FAB) m/e 591.2(M+1, 100); Anal. C33 H42 N4 O6; C, H, N. Patent; Warner-Lambert Company; US5278316; (1994); (A1) English View in Reaxys ...ethylthiazoline, 2-isobutyl-4,5-dimethyl-3-thiazoline, 4-methylthiazole, 2-methylthiazole, 2-acetyl-2-thiazole, 2,4,5trimethylthiazole, 2,4-dimethyl-5-ethylthiazole, 5-hydroxyethyl-4-methylthiazole, 1,3-benzothiazole, 1,3-thiazolidine, 2-methyl-1,3- thiazolidine, 2-isopropyl-1,3-thiazolidine, ... 2-methylpropanal, 2-methybutanal, 3-methylbutanal, 4-pentenal, (E)-2-nonenal, hexanal, (E)-2-hexenal, 2,4-hexadienal, heptanal, 4-heptenal, octanal, (E)-2-octenal, octadienal, nonanal, (E,E)-2,4-nonadienal, (2E,6Z)-nonadienal, (E,E)-2,4-decadienal, (E,Z)-2,4-decadienal, (E)-2-undecenal, 12-methyl-tridecanal, 3-methyl-1-butanol, 1-pentanol, 1-penten-3-ol, 3-cis-hexenol, 3-methyl-2-hexen-1-ol, 1-heptanol, 3-octanol, 1-octene-3-ol, 3-hydroxy-2-butanone, 2-butanone, 2,3-butanedione, 2-pentanone, methyl isobutyl ketone, 1-pentene-3-one, 2-hexanone, oct-1-en-3-one, 2,3-octanedione, 2-nonanone, 2-decanone, 4-undecanone, 2-tridecanone, 3-methylcyclopentanone, 3-methylcyclopentenone, methyl cyclopentenolone, dimethyl cyclopentenolone, ethyl cyclopentenolone, gamma-hexalactone, gamma-octalactone, gamma-decalactone, gamma-dodecalactone, delta-nonalactone, butyric acid, isobutyric acid, isovaleric acid, pentanoic acid, hexanoic acid, isocaproic acid, heptanoic acid, Patent; IMAX Discovery GmbH; WINNING, Marcel; LOHMER, Stefan; PEVARELLO, Paolo; EP2832233; (2015); (A1) English View in Reaxys Patent; IMAX Discovery GmbH; WINNING, Marcel; LOHMER, Stefan; PEVARELLO, Paolo; EP2832234; (2015); (A1) English View in Reaxys ...line, 2-isobutyl-4,5-dimethyl-3-thiazoline, 4-methylthiazole, 2-methylthiazole, 2-acetyl-2-thiazole, 2,4,5-trimethylthiazole, 2,4-dimethyl-5-ethylthiazole, 5-hydroxyethyl-4-methylthiazole (sulfurol), 1,3-benzothiazole, 1,3-thiazolidine, 2methyl-1,3- thiazolidine, 2-isopropyl-1,3-thiazolidine,

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... 2-methylpropanal, 2-methybutanal, 3-methylbutanal, 4-pentenal, (E)-2-nonenal, hexanal, (E)-2-hexenal, 2,4-hexadienal, heptanal, 4-heptenal, octanal, (E)-2-octenal, octadienal, nonanal, (E,E)-2,4-nonadienal, (2E,6Z)-nonadienal, (E,E)-2,4-decadienal, (E,Z)-2,4-decadienal, (E)-2-undecenal, 12-methyl-tridecanal, 3-methyl-1-butanol, 1-pentanol, 1-penten-3-ol, 3-cis-hexenol, 3-methyl-2-hexen-1-ol, 1-heptanol, 3-octanol, 1-octene-3-ol, 3-hydroxy-2-butanone (acetoin), 2-butanone, 2,3-butanedione (diacetyl), 2-pentanone, methyl isobutyl ketone, 1pentene-3-one, 2-hexanone, oct-1-en-3-one, 2,3-octanedione, 2-nonanone, 2-decanone, 4-undecanone, 2-tridecanone, 3-methylcyclopentanone, 3-methylcyclopentenone, methyl cyclopentenolone (3-methyl-1,2-cyclopentanedione), dimethyl cyclopentenolone (3,4-dimethyl-1,2-cyclopentanedione, 3,5-dimethyl-1,2-cyclopentanedione), ethyl cyclopentenolone (3-ethyl-1,2-cyclopentanedione), gamma-hexalactone, gamma-octalactone, gamma-decalactone, gamma-dodecalactone, delta-nonalactone, butyric acid, isobutyric acid, isovaleric acid, pentanoic acid, hexanoic acid, isocaproic acid, heptanoic acid, Patent; IMAX Discovery GmbH; WINNING, Marcel; LOHMER, Stefan; PEVARELLO, Paolo; EP2832233; (2015); (A1) English View in Reaxys ...line, 2-isobutyl-4,5-dimethyl-3-thiazoline, 4-methylthiazole, 2-methylthiazole, 2-acetyl-2-thiazole, 2,4,5-trimethylthiazole, 2,4-dimethyl-5-ethylthiazole, 5-hydroxyethyl-4-methylthiazole (sulfurol), 1,3-benzothiazole, 1,3-thiazolidine, 2methyl-1,3- thiazolidine, 2-isopropyl-1,3-thiazolidine, ... gamma-octalactone, gamma-decalactone, gamma-dodecalactone, delta-nonalactone, butyric acid, isobutyric acid, isovaleric acid, pentanoic acid, ... Patent; IMAX Discovery GmbH; WINNING, Marcel; LOHMER, Stefan; PEVARELLO, Paolo; EP2832234; (2015); (A1) English View in Reaxys

HO O

Rx-ID: 9941109 View in Reaxys 31/804 Yield 90 %

Conditions & References With enzyme from Synechocystis sp. PCC 6803 in phosphate buffer, Time= 12h, T= 30 °C , pH= 7.2 Mukherjee, Chandrani; Zhu, Dunming; Biehl, Edward R.; Hua, Ling; European Journal of Organic Chemistry; nb. 23; (2006); p. 5238 - 5242 View in Reaxys

83 %

With benzene-1,2-dicarboxylic acid, Time= 0.666667h, microwave irradiation Bratulescu, George; Revue Roumaine de Chimie; vol. 50; nb. 3; (2005); p. 161 - 163 View in Reaxys With chaetomium globosum (Q2GR86), water, Enzymatic reaction, Reagent/catalyst Black, Gary W.; Brown, Nicola L.; Perry, Justin J. B.; Randall, P. David; Turnbull, Graeme; Zhang, Meng; Chemical Communications; vol. 51; nb. 13; (2015); p. 2660 - 2662 View in Reaxys With nitrilase from Gordonia terrae in aq. phosphate buffer, Time= 1h, T= 35 °C , pH= 8, Enzymatic reaction Kumar, Vijay; Seth, Amit; Kumari, Vijaya; Kumar, Virender; Bhalla, Tek C.; Protein and Peptide Letters; vol. 22; nb. 1; (2015); p. 52 - 62 View in Reaxys

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O N

O O

Rx-ID: 25984094 View in Reaxys 32/804 Yield

Conditions & References With Cys9 Ala/Asp11 Cys in water, Enzyme kinetics, Further Variations: Catalysts Taglieber, Andreas; Hoebenreich, Horst; Carballeira, J. Daniel; Mondiere, Regis J. G.; Reetz, Manfred T.; Angewandte Chemie - International Edition; vol. 46; nb. 45; (2007); p. 8597 - 8600 View in Reaxys With tHisF in water Taglieber, Andreas; Hoebenreich, Horst; Carballeira, J. Daniel; Mondiere, Regis J. G.; Reetz, Manfred T.; Angewandte Chemie - International Edition; vol. 46; nb. 45; (2007); p. 8597 - 8600 View in Reaxys With Aspergillus oryzae cutinase, glycerol in methanol, pH= 7.5, aq. buffer, Enzymatic reaction, Kinetics, Reagent/ catalyst Zhiqiang, Liu; Gosser, Yuying; Baker, Peter James; Ravee, Yaniv; Ziying, Lu; Alemu, Girum; Huiguang, Li; Butterfoss, Glenn L.; Kong, Xiang-Peng; Gross, Richard; Montclare, Jin Kim; Journal of the American Chemical Society; vol. 131; nb. 43; (2009); p. 15711 - 15716 View in Reaxys With Aspergillus niger lipase AS Amano in dimethyl sulfoxide, T= 40 °C , pH= 5, aq. buffer, Enzymatic reaction, Kinetics, Reagent/catalyst Baba, Akiko; Yoshioka, Tadao; Journal of Molecular Catalysis B: Enzymatic; vol. 69; nb. 1-2; (2011); p. 74 - 82 View in Reaxys With REBr enzyme, water, T= 40 °C , pH= 8.5, Enzymatic reaction, Kinetics, Concentration Beloqui, Ana; Polaina, Julio; Vieites, Jose Maria; Reyes-Duarte, Dolores; Torres, Rodrigo; Golyshina, Olga V.; Chernikova, Tatyana N.; Waliczek, Agnes; Aharoni, Amir; Yakimov, Michail M.; Timmis, Kenneth N.; Golyshin, Peter N.; Ferrer, Manuel; ChemBioChem; vol. 11; nb. 14; (2010); p. 1975 - 1978 View in Reaxys With Rhodococcus sp. LKE-028 esterase, T= 70 °C , pH= 11, aq. buffer, Enzymatic reaction Kumar, Lokendra; Singh, Balvinder; Adhikari, Dilip Kumar; Mukherjee, Joydeep; Ghosh, Debashish; Process Biochemistry; vol. 47; nb. 6; (2012); p. 983 - 991 View in Reaxys 2.7 Biochemical characterisation General procedure: To investigate substrate specificity of Est22, enzyme activity was determined using standard esterase assay in the presence of 1mM of the specified p-nitrophenyl esters of various chain lengths: p-nitrophenyl acetate (C2), p-nitrophenyl butyrate (C4), p-nitrophenyl caprylate (C8) and p-nitrophenyl laurate (C12). Optimum temperature of the Est22 was determined by measuring the rate of p-nitrophenyl butyrate hydrolysis over a temperature range (30–70°C). Where necessary the pH adjustments at set temperatures were performed to take into account the effect that changing temperature has on pH. A thermostability profile of Est22 was generated by incubating the enzyme at three temperature points 30-, 50- and 70°C, followed by measuring residual activities after every 30min using the standard esterase assay. The influence of pH on the p-nitrophenyl butyrate hydrolysis was tested from pH 4.0–9.5 at 30°C. With Est22 esterase in aq. buffer, T= 30 °C , pH= 7.5, Enzymatic reaction Mokoena, Nobalanda; Mathiba, Kgama; Tsekoa, Tsepo; Steenkamp, Paul; Rashamuse, Konanani; Biochemical and Biophysical Research Communications; vol. 437; nb. 3; (2013); p. 342 - 348 View in Reaxys With lipase, Enzymatic reaction

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Sengupta, Samudra; Patra, Debabrata; Ortiz-Rivera, Isamar; Agrawal, Arjun; Shklyaev, Sergey; Dey, Krishna K.; Cordova-Figueroa, Ubaldo; Mallouk, Thomas E.; Sen, Ayusman; Nature Chemistry; vol. 6; nb. 5; (2014); p. 415 - 422 View in Reaxys With Penicillium expansum lipase T66L/D70N mutant, T= 35 °C , pH= 7, Enzymatic reaction, Reagent/catalyst Tang, Lianghua; Su, Min; Yan, Junzhe; Xie, Sheng; Zhang, Wenhuang; Process Biochemistry; vol. 50; nb. 8; (2015); p. 1218 - 1223 View in Reaxys

O O

Rx-ID: 32781042 View in Reaxys 33/804 Yield

Conditions & References With potassium chloride, water, sodium chloride, calcium chloride, magnesium chloride, N-2-hydroxyethylpiperazineN'-2-ethanesulfonic acid in methanol, pH= 7.2, UV-irradiation, Kinetics Soares, Ana M. S.; Piloto, Ana M.; Hungerford, Graham; Costa, Susana P. G.; Goncalves, M. Sameiro T.; European Journal of Organic Chemistry; nb. 5; (2012); p. 922 - 930 View in Reaxys in acetonitrile, Time= 4.63333h, Photolysis, Wavelength, Time Piloto, Ana M.; Hungerford, Graham; Sutter, Jens U.; Soares, Ana M.S.; Costa, Susana P.G.; Goncalves, M. Sameiro T.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 299; (2015); p. 44 - 53 View in Reaxys

O C

HO O

Rx-ID: 39250954 View in Reaxys 34/804 Yield

Conditions & References 2.3. General procedure of glycerol carbonylation General procedure: carbonylationA 50 mL high-pressure reactor was charged with AcOH (6.7 mL),glycerol (27 mmol), H2O (1.5 mL), HI (57 wtpercent, 13 mmol) and poly-mer anchored rhodium catalyst (25 mol) were taken into reactor.The reactor was then purged with CO for about 5 min and thenpressurized with CO gas (30 bar). The carbonylation reactions werecarried out at 180C for 5 h. The products were collected and ana-lyzed by GC and NMR. With hydrogen iodide, acetic acid in water, Time= 5h, T= 180 °C , p= 22502.3Torr Molla, Rostam Ali; Ghosh, Kajari; Roy, Anupam Singha; Islam, Sk. Manirul; Journal of Molecular Catalysis A: Chemical; vol. 396; (2014); p. 268 - 274 View in Reaxys

67 %Chro- With hydrogen iodide, acetic acid in water, Time= 5h, T= 180 °C , p= 22502.3Torr , Temperature mat., 31 %Chromat. Molla, Rostam Ali; Ghosh, Kajari; Roy, Anupam Singha; Islam, Sk. Manirul; Journal of Molecular Catalysis A: Chemical; vol. 396; (2015); p. 268 - 274 View in Reaxys

OH OH

HO O

Rx-ID: 39250955 View in Reaxys 35/804 Yield

Conditions & References 2.3. General procedure of glycerol carbonylation

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General procedure: carbonylationA 50 mL high-pressure reactor was charged with AcOH (6.7 mL),glycerol (27 mmol), H2O (1.5 mL), HI (57 wtpercent, 13 mmol) and poly-mer anchored rhodium catalyst (25 mol) were taken into reactor.The reactor was then purged with CO for about 5 min and thenpressurized with CO gas (30 bar). The carbonylation reactions werecarried out at 180C for 5 h. The products were collected and ana-lyzed by GC and NMR. With hydrogen iodide, acetic acid in water, Time= 5h, T= 130 °C , p= 22502.3Torr Molla, Rostam Ali; Ghosh, Kajari; Roy, Anupam Singha; Islam, Sk. Manirul; Journal of Molecular Catalysis A: Chemical; vol. 396; (2014); p. 268 - 274 View in Reaxys 14 %Chromat.

2.3. General procedure of glycerol carbonylation General procedure: A 50 mL high-pressure reactor was charged with AcOH (6.7 mL),glycerol (27 mmol), H2O (1.5 mL), HI (57 wtpercent, 13 mmol) and poly-mer anchored rhodium catalyst (25 mol) were taken into reactor.The reactor was then purged with CO for about 5 min and thenpressurized with CO gas (30 bar). The carbonylation reactions werecarried out at 180C for 5 h. The products were collected and ana-lyzed by GC and NMR. With hydrogen iodide, acetic acid in water, Time= 5h, T= 130 °C , p= 22502.3Torr Molla, Rostam Ali; Ghosh, Kajari; Roy, Anupam Singha; Islam, Sk. Manirul; Journal of Molecular Catalysis A: Chemical; vol. 396; (2015); p. 268 - 274 View in Reaxys

OH OH

Rx-ID: 39259324 View in Reaxys 36/804 Yield

Conditions & References

7 %Chromat.

2.3. General procedure of glycerol carbonylation General procedure: A 50 mL high-pressure reactor was charged with AcOH (6.7 mL),glycerol (27 mmol), H2O (1.5 mL), HI (57 wtpercent, 13 mmol) and poly-mer anchored rhodium catalyst (25 mol) were taken into reactor.The reactor was then purged with CO for about 5 min and thenpressurized with CO gas (30 bar). The carbonylation reactions werecarried out at 180C for 5 h. The products were collected and ana-lyzed by GC and NMR. With hydrogen iodide, acetic acid in water, Time= 5h, T= 180 °C , p= 22502.3Torr Molla, Rostam Ali; Ghosh, Kajari; Roy, Anupam Singha; Islam, Sk. Manirul; Journal of Molecular Catalysis A: Chemical; vol. 396; (2015); p. 268 - 274 View in Reaxys

O O

Rx-ID: 39603185 View in Reaxys 37/804 Yield

Conditions & References Photolysis - general General procedure: A 1 x 10-4m methanol or acetonitrile/HEPES (80:20) solution of compounds 7–15 (5 mL) were placed in a quartz tube and irradiated in a Rayonet RPR-100 reactor at the desired wavelength. The lamps used for irradiation were at 254, 300, 350 and 419±10 nm. HEPES buffer solution was prepared in distilled water with HEPES (4-(2-hydroxyethyl)-1-piperazine ethanesulfonic acid)(10 mM), sodium chloride (120 mM), potassium chloride(3 mM), calcium chloride (1 mM) and magnesium chloride(1 mM) and pH adjusted to 7.2 with aqueous 1 M sodium hydroxide solution. in acetonitrile, Time= 0.233333h, Photolysis, Solvent, Wavelength, Time Piloto, Ana M.; Hungerford, Graham; Sutter, Jens U.; Soares, Ana M.S.; Costa, Susana P.G.; Goncalves, M. Sameiro T.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 299; (2015); p. 44 - 53 View in Reaxys

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O O

Rx-ID: 39603186 View in Reaxys 38/804 Yield

Conditions & References in acetonitrile, Time= 0.966667h, Photolysis, Solvent, Wavelength, Time Piloto, Ana M.; Hungerford, Graham; Sutter, Jens U.; Soares, Ana M.S.; Costa, Susana P.G.; Goncalves, M. Sameiro T.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 299; (2015); p. 44 - 53 View in Reaxys O O

Rx-ID: 39603187 View in Reaxys 39/804 Yield

Conditions & References in acetonitrile, Time= 3.1h, Photolysis, Solvent, Wavelength, Time Piloto, Ana M.; Hungerford, Graham; Sutter, Jens U.; Soares, Ana M.S.; Costa, Susana P.G.; Goncalves, M. Sameiro T.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 299; (2015); p. 44 - 53 View in Reaxys O O

Rx-ID: 39603189 View in Reaxys 40/804 Yield

Conditions & References in acetonitrile, Time= 7.61667h, Photolysis, Solvent, Wavelength, Time Piloto, Ana M.; Hungerford, Graham; Sutter, Jens U.; Soares, Ana M.S.; Costa, Susana P.G.; Goncalves, M. Sameiro T.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 299; (2015); p. 44 - 53 View in Reaxys O O O O

Rx-ID: 39603197 View in Reaxys 41/804 Yield

Conditions & References in acetonitrile, Time= 0.0833333h, Photolysis, Solvent, Wavelength, Time Piloto, Ana M.; Hungerford, Graham; Sutter, Jens U.; Soares, Ana M.S.; Costa, Susana P.G.; Goncalves, M. Sameiro T.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 299; (2015); p. 44 - 53 View in Reaxys

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O S

Rx-ID: 39603198 View in Reaxys 42/804 Yield

Conditions & References in acetonitrile, Time= 0.883333h, Photolysis, Solvent, Wavelength, Time Piloto, Ana M.; Hungerford, Graham; Sutter, Jens U.; Soares, Ana M.S.; Costa, Susana P.G.; Goncalves, M. Sameiro T.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 299; (2015); p. 44 - 53 View in Reaxys O S

Rx-ID: 39603199 View in Reaxys 43/804 Yield

Conditions & References in acetonitrile, Time= 2.55h, Photolysis, Solvent, Wavelength, Time Piloto, Ana M.; Hungerford, Graham; Sutter, Jens U.; Soares, Ana M.S.; Costa, Susana P.G.; Goncalves, M. Sameiro T.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 299; (2015); p. 44 - 53 View in Reaxys O S

O O

Rx-ID: 39603200 View in Reaxys 44/804 Yield

Conditions & References in acetonitrile, Time= 0.95h, Photolysis, Solvent, Wavelength, Time Piloto, Ana M.; Hungerford, Graham; Sutter, Jens U.; Soares, Ana M.S.; Costa, Susana P.G.; Goncalves, M. Sameiro T.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 299; (2015); p. 44 - 53 View in Reaxys

Rx-ID: 39755306 View in Reaxys 45/804 Yield

Conditions & References With di-tert-butyl peroxide, 1,2-Dinitrobenzene, benzene, Time= 12h, T= 150 °C , Inert atmosphere, Sealed tube Tang, Ren-Jin; He, Qing; Yang, Luo; Chemical Communications; vol. 51; nb. 27; (2015); p. 5925 - 5928 View in Reaxys

O HO

Rx-ID: 40066587 View in Reaxys 46/804

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Yield

Conditions & References A sample of 1 (12.0 mg) was stirred for 1 h with aqueous solution of KMnO4 (1percent). The reaction products were acidified with concentrated HCl and extracted with Et2O to afford free fatty acids (9.0 mg). This material was esterified with CH2N2 and subjected to CG-LREIMS analysis. With potassium permanganate in water, Time= 1h Santos, Luciana de Á.; Cavalheiro, Alberto J.; Tempone, Andre G.; Correa, Daniela S.; Alexandre, Tatiana R.; Quintiliano, Natalia F.; Rodrigues-Oliveira, AndréF; Oliveira-Silva, Diogo; Martins, Roberto Carlos C.; Lago, João Henrique G.; Molecules; vol. 20; nb. 5; (2015); p. 8168 - 8180 View in Reaxys

O O

Rx-ID: 40094722 View in Reaxys 47/804 Yield

Conditions & References With oxygen in water, Time= 6h, T= 100 °C , p= 2250.23Torr Gandarias, Inaki; Miedziak, Peter J.; Nowicka, Ewa; Douthwaite, Mark; Morgan, David J.; Hutchings, Graham J.; Taylor, Stuart H.; ChemSusChem; vol. 8; nb. 3; (2015); p. 473 - 480 View in Reaxys O HO

Rx-ID: 40192895 View in Reaxys 48/804 Yield 29 %

Conditions & References With Pd/C in water, Time= 6h, T= 250 °C , p= 4500.45Torr , Inert atmosphere De Schouwer, Free; Claes, Laurens; Claes, Nathalie; Bals, Sara; Degrève, Jan; De Vos, Dirk E.; Green Chemistry; vol. 17; nb. 4; (2015); p. 2263 - 2270 View in Reaxys

Cl O

Rx-ID: 40402546 View in Reaxys 49/804 Yield 77 %

Conditions & References With water, triethylamine in chloroform, Time= 0.0222222h Britton, Joshua; Chalker, Justin M.; Raston, Colin L.; Chemistry - A European Journal; vol. 21; nb. 30; (2015); p. 10660 - 10665 View in Reaxys

O O

O HO

OH O

HO O

Rx-ID: 40558900 View in Reaxys 50/804 Yield 51 %, 32 %

Conditions & References With dihydrogen peroxide in acetonitrile, Time= 12h, Irradiation Mohamed, Mohamed Mokhtar; RSC Advances; vol. 5; nb. 57; (2015); p. 46405 - 46414

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View in Reaxys

O O

H N

Rx-ID: 40756639 View in Reaxys 51/804 Yield

Conditions & References in methanol, aq. phosphate buffer, Irradiation, Photolysis Soares, Ana M. S.; Hungerford, Graham; Costa, Susana P. G.; Gonçalves, M. Sameiro T.; New Journal of Chemistry; vol. 39; nb. 9; (2015); p. 7227 - 7233 View in Reaxys

O O

Rx-ID: 40756640 View in Reaxys 52/804 Yield

O O

NH 2

Rx-ID: 40756649 View in Reaxys 53/804 Yield

O O

H N

HO O

Rx-ID: 40756650 View in Reaxys 54/804 Yield

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O O

Rx-ID: 40756651 View in Reaxys 55/804 Yield

N HO

O O

Rx-ID: 40901862 View in Reaxys 56/804 Yield

Conditions & References in methanol, Time= 1.05833h, pH= 7.2, Irradiation, Quantum yield, Wavelength Soares, Ana M. S.; Hungerford, Graham; Costa, Susana P. G.; Gonçalves, M. Sameiro T.; European Journal of Organic Chemistry; vol. 2015; nb. 27; (2015); p. 5979 - 5986 View in Reaxys NH 2 O HO

O O

Rx-ID: 40901869 View in Reaxys 57/804 Yield

Conditions & References in methanol, Time= 0.275h, pH= 7.2, Irradiation, Quantum yield, Wavelength Soares, Ana M. S.; Hungerford, Graham; Costa, Susana P. G.; Gonçalves, M. Sameiro T.; European Journal of Organic Chemistry; vol. 2015; nb. 27; (2015); p. 5979 - 5986 View in Reaxys

HN O

O O

Rx-ID: 40901870 View in Reaxys 58/804 Yield

Conditions & References in methanol, Time= 0.123333h, pH= 7.2, Irradiation, Quantum yield, Wavelength Soares, Ana M. S.; Hungerford, Graham; Costa, Susana P. G.; Gonçalves, M. Sameiro T.; European Journal of Organic Chemistry; vol. 2015; nb. 27; (2015); p. 5979 - 5986 View in Reaxys

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N O

O O

Rx-ID: 40901871 View in Reaxys 59/804 Yield

Conditions & References in methanol, Time= 0.466667h, pH= 7.2, Irradiation, Quantum yield, Wavelength Soares, Ana M. S.; Hungerford, Graham; Costa, Susana P. G.; Gonçalves, M. Sameiro T.; European Journal of Organic Chemistry; vol. 2015; nb. 27; (2015); p. 5979 - 5986 View in Reaxys

HN HO

O O

Rx-ID: 40901872 View in Reaxys 60/804 Yield

Conditions & References in methanol, Time= 0.28h, pH= 7.2, Irradiation, Quantum yield, Wavelength Soares, Ana M. S.; Hungerford, Graham; Costa, Susana P. G.; Gonçalves, M. Sameiro T.; European Journal of Organic Chemistry; vol. 2015; nb. 27; (2015); p. 5979 - 5986 View in Reaxys

O HO

O OH

HO O

Rx-ID: 40902921 View in Reaxys 61/804 Yield

Conditions & References Catalytic hydrogenation of IA was performed in a 50 ml autoclave. After 1 wt.percent IA aqueous solution and 1.5 molpercent Pd catalysts were introduced into the reactor, the reactor was purged with H2 for five times and then pressurized to the desired pressure at room temperature. After reaction, unconsumed IA was detected by high performance liquid chromatography (HPLC) and products were quantified by gas chromatography (GC). The products were also analyzed by GC or LC coupled with a mass spectrometer (MS). With hydrogen in water, Time= 20h, T= 200 °C , p= 30003Torr , Autoclave Li, Sha; Wang, Xicheng; Liu, Xiaoran; Xu, Guoqiang; Han, Sheng; Mu, Xindong; Catalysis Communications; vol. 61; nb. 1; (2015); p. 92 - 96 View in Reaxys

O O

O HO

HO O

Rx-ID: 41670129 View in Reaxys 62/804 Yield

Conditions & References With palladium on activated charcoal, hydrogen, Time= 20h, T= 200 °C , p= 37503.8Torr , Autoclave Liu, Xiaoran; Wang, Xicheng; Xu, Guoqiang; Liu, Qiang; Mu, Xindong; Liu, Haichao; Journal of Materials Chemistry A; vol. 3; nb. 46; (2015); p. 23560 - 23569 View in Reaxys

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OH O

Rx-ID: 43559993 View in Reaxys 63/804 Yield

Conditions & References

32 %Chro- Oxidation of primary alkanols 1a—h with H2O2—HBr in methanol or in a water—methanol mixture (general mat., 65 procedure). %Chromat. General procedure: To a vigorously stirred solution of alkanol 1 (1 mmol) in 48percent HBr in MeOH or MeOH—H2O, a solution of H2O2 (35percent) in the corresponding solvent (1—1.5 mL) was added by portions (0.2—0.25 mL) at 65—70 °C (the reagent molar ratios are given in Tables 3 and 4). After addition of the first portion of the H2O2 solution, the reaction mixture turned to light yellow and after 20—30 min was colorless. Then the next portion of hydrogen peroxide was added. After completion of the reaction, the mixture was cooled, extracted with diethyl ether (3×15 mL), the combined organic layers were washed with water, dried with MgSO4, and the solvent was removed in vacuo. The conversions of alkanols and the product yields were determined by GC. With water, hydrogen bromide, dihydrogen peroxide, T= 65 - 70 °C Nikishin; Sokova; Terent´ev; Kapustina; Russian Chemical Bulletin; vol. 64; nb. 12; (2015); p. 2845 - 2850; Izv. Akad. Nauk, Ser. Khim.; nb. 12; (2015); p. 2845 - 2850,6 View in Reaxys O

O HO

O O

Rx-ID: 44196200 View in Reaxys 64/804 Yield

Conditions & References 7-1 : Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below. With palladium on activated carbon, hydrogen in 1,4-dioxane, Time= 4h, T= 250 °C , p= 3800.26Torr , Reagent/catalyst, Pressure Patent; CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO; (40 pag.); KR2015/118287; (2015); (A) Korean View in Reaxys

O O

HO OH O

Rx-ID: 44196201 View in Reaxys 65/804 Yield

Conditions & References 7-1 : Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below. With Re/Ac, hydrogen in 1,4-dioxane, Time= 25h, T= 250 °C , p= 3800.26Torr Patent; CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO; (40 pag.); KR2015/118287; (2015); (A) Korean View in Reaxys

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O HO

HO OH

O O

Rx-ID: 44196202 View in Reaxys 66/804 Yield

Conditions & References 7-3 : Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone General procedure: The procedure of Example 7-1 was repeated except that Rh (5) Re (5) / SiO2 was used as the catalyst, and the results are shown in Table 25 below. Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below. With hydrogen in 1,4-dioxane, Time= 5h, T= 250 °C , p= 3800.26Torr Patent; CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO; (40 pag.); KR2015/118287; (2015); (A) Korean View in Reaxys

O O

O HO

Rx-ID: 44196203 View in Reaxys 67/804 Yield

Conditions & References 7-3 : Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone General procedure: The procedure of Example 7-1 was repeated except that Rh (5) Re (5) / SiO2 was used as the catalyst, and the results are shown in Table 25 below. Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below. With hydrogen in 1,4-dioxane, Time= 9.5h, T= 250 °C , p= 3800.26Torr , Time Patent; CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO; (40 pag.); KR2015/118287; (2015); (A) Korean View in Reaxys

O O

HO O

Rx-ID: 44196204 View in Reaxys 68/804 Yield

Conditions & References 7-5 : Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and 2 g of Rh (5) Re (5) / SiO2 (HISIL233) was used as the catalyst.- feed: 50/50 vol percent HO-GBL / 1,4-dioxane, H2 / HO-GBL = 50/1, WHSV: 0.3h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 27 below. With hydrogen in 1,4-dioxane, Time= 15h, T= 250 °C , p= 3800.26Torr Patent; CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO; (40 pag.); KR2015/118287; (2015); (A) Korean

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View in Reaxys O

O O

Rx-ID: 44196205 View in Reaxys 69/804 Yield

Conditions & References 7-5 : Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and 2 g of Rh (5) Re (5) / SiO2 (HISIL233) was used as the catalyst.- feed: 50/50 vol percent HO-GBL / 1,4-dioxane, H2 / HO-GBL = 50/1, WHSV: 0.3h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 27 below. With hydrogen in 1,4-dioxane, Time= 25h, T= 250 °C , p= 3800.26Torr Patent; CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO; (40 pag.); KR2015/118287; (2015); (A) Korean View in Reaxys

HO OH

Rx-ID: 37629008 View in Reaxys 70/804 Yield

Conditions & References With iodoacetate spiropyran modified-Bacillus thermocathenolatus lipase 2 at positon 245 immobilized on transparent agarose microspheres, UV-irradiation Bautista-Barrufet, Antoni; Lopez-Gallego, Fernando; Rojas-Cervellera, Victor; Rovira, Carme; Pericas, Miquel A.; Guisan, Jose M.; Gorostiza, Pau; ACS Catalysis; vol. 4; nb. 3; (2014); p. 1004 - 1009 View in Reaxys

HO HO

Rx-ID: 38329028 View in Reaxys 71/804 Yield 14.9 %, 18.2 %, 32.5 %

Conditions & References 2.2 General reaction conditions General procedure: For our investigations we utilized the reaction conditions previously identified to be suitable for the P. furiosus-catalyzed hydrogenation of carboxylic acids [6]. In short: reaction mixtures of 2 ml in 16 ml autoclaves containing 0.3 g P. furiosus frozen cells, 10 mM carboxylic acid substrate and 100 mM sodium phosphate buffer (pH 6.5) were flushed with N2 and pre-purged with H2 (p=5 bar). A photograph of the experimental setup is shown in the supporting information. The reactions were incubated at 40 °C with magnetic agitation at 100 rpm for 24 h. The reaction mixture was acidified to pH 2.0 with 5N HCl, extracted twice with distilled ethyl acetate or diethyl ether containing 1-octanol or n-decane as an internal standard, and analyzed by GC. In the case of some aromatic acids, the samples were centrifuged for 15 min at 13,000 rpm after adding equal volumes of acetonitrile, and the supernatant was analyzed by HPLC. With hydrogen in aq. phosphate buffer, Time= 24h, T= 40 °C , p= 3750.38Torr , pH= 6.5, Autoclave, chemoselective reaction Ni, Yan; Hagedoorn, Peter-Leon; Xu, Jian-He; Arends, Isabel W.C.E.; Hollmann, Frank; Journal of Molecular Catalysis B: Enzymatic; vol. 103; (2014); p. 52 - 55 View in Reaxys

Rx-ID: 38594962 View in Reaxys 72/804

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Yield

Conditions & References With dihydrogen peroxide, Time= 6h, T= 80 °C , Dean-Stark, Catalytic behavior Singh, Sukriti; Patel, Anjali; Catalysis Letters; vol. 144; nb. 9; (2014); p. 1557 - 1567,11 View in Reaxys

Rx-ID: 38699457 View in Reaxys 73/804 Yield

Conditions & References With 2O39PW11 (7-)*11K(1+)*Pr(3+)*22H2O, dihydrogen peroxide in water, Time= 3h, T= 90 °C , Green chemistry Saini, Mukesh Kumar; Gupta, Rakesh; Parbhakar, Swati; Singh, Surendra; Hussain, Firasat; RSC Advances; vol. 4; nb. 72; (2014); p. 38446 - 38449 View in Reaxys Rx-ID: 38943499 View in Reaxys 74/804

Yield

Conditions & References With hydrogen, T= 244.84 °C , p= 46579.7Torr Patent; Wisconsin Alumni Research Foundation; Huber, George W.; Kim, Yong Tae; US2014/275638; (2014); (A1) English View in Reaxys Rx-ID: 38943500 View in Reaxys 75/804

Yield

Conditions & References With hydrogen, T= 244.84 °C , p= 46579.7Torr Patent; Wisconsin Alumni Research Foundation; Huber, George W.; Kim, Yong Tae; US2014/275638; (2014); (A1) English View in Reaxys

O P

Rx-ID: 39375769 View in Reaxys 76/804 Yield

Conditions & References With water, nitric acid in N-dodecane, Autoclave, Heating, Activation energy, Solvent Sreekantan, Smitha Velayuthan; Mahadevan, Surianarayanan; Jala, Samuel Vara Kumar; Seshadri, Hariharan; Mandal, Asit Baran; Organic Process Research and Development; vol. 18; nb. 12; (2014); p. 1821 - 1827 View in Reaxys

O OH

HO O

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O HO O

O E

OH OH

HO O

Rx-ID: 39884724 View in Reaxys 77/804 Yield

Conditions & References With water, Time= 504h, Acidic conditions, pH-value, Reagent/catalyst Rakete, Stefan; Berger, Robert; Böhme, Steffi; Glomb, Marcus A.; Journal of Agricultural and Food Chemistry; vol. 62; nb. 30; (2014); p. 7541 - 7549 View in Reaxys

OH O

Rx-ID: 34805875 View in Reaxys 78/804 Yield

Conditions & References General procedure: The oxidations of gaseous alkanes with H2O2 were carried out in a13 mL stainless steel autoclave, equipped with a Teflon-coated magneticstirring bar. In a typical experiment, after additions of all liquid reagents in the form of stock solutions in acetonitrile, the autoclavewas closed and pressurized with gaseous alkane (typically 20.0, 6.0or 0.7 atm of CH4 and C2H6, C3H8 or n-C4H10, respectively). The reaction mixture was stirred for 4 h at 50 °C using a magnetic stirrer andan oil bath, whereupon it was cooled in an ice bath, degassed, openedand transferred to a flask for GC analysis. With 2-carboxypyrazine, (C5H5)Fe(C5H5), dihydrogen peroxide, triphenylphosphine in acetonitrile, Time= 4h, T= 50 °C , Autoclave, Overall yield = 58 percent Shul'pin, Georgiy B.; Kirillova, Marina V.; Shul'pina, Lidia S.; Pombeiro, Armando J.L.; Karslyan, Eduard E.; Kozlov, Yuriy N.; Catalysis Communications; vol. 31; (2013); p. 32 - 36 View in Reaxys 2.5. Peroxidative oxidation of alkanes General procedure: The alkane oxidations were typically carried out in air in thermostated (50° C) Pyrex cylindrical vessels or round bottom flasks with vigorous stirring and using MeCN as solvent (up to 5.0 mL totalvolume). Typically, the catalyst precursor 1 was introduced intothe reaction mixture in the form of a stock solution in acetonitrile(2.5×10−4 M). Then PCA (optional) was added as a solid or in theform of a stock solution in MeCN (0.44 M). The alkane substrate, typically cyclohexane (0.25 mL, 2.3 mmol) was then introduced, andthe reaction started when hydrogen peroxide (50percent in H2O, 0.68 mL,11 mmol) was added in one portion. The final concentrations of the reactants in the reaction mixture were as follows: catalystprecursor 1 (5×10−6 −5×10−4 M), PCA (0−0.005 M), substrate(0.46 M) and H2O2 (2.2 M). The samples were analysed by GC using nitromethane (0.05 mL) as an internal standard. Attribution of peaks was made by comparison with chromatograms of authenticsamples. Chromatographic analyses were undertaken by usinga Fisons Instruments GC 8000 series gas chromatograph (He ascarrier gas) with a BP20/SGE (30 m×0.22 mm×0.25 m) capillarycolumn (FID detector) and the Jasco-Borwin v.1.50 software. Since the oxygenation of alkanes often gives rise to the formationof the corresponding alkyl hydroperoxides as the main primaryproducts, the quantification was performed by a method developedby Shul’pin [12–14]. For precise determination of oxygenate concentrations only data obtained after reductions of the reactionsample with PPh3 were usually used, taking into account that theoriginal reaction mixture typically contained the three products:alkyl hydroperoxide (as the primary product), ketone and alcohol.The oxidations of gaseous alkanes were carried out in a 13 mLstainless steel autoclave, equipped with a Teflon-coated magneticstirring bar. In a typical experiment, after additions of all liquid (inthe form of stock solutions in acetonitrile) and solid reagents, theautoclave was closed and pressurized with 0.7–20.0 atm of gaseous alkane (typically 20.0, 6.0, or 0.7 atm of CH4 and C2H6, C3H8, or n-C4H10, respectively). The reaction mixture was stirred for 4 h at 50° C using a magnetic stirrer and an oil bath, whereupon it wascooled in an ice bath, degassed, opened and transferred to a flaskfor GC analysis. In the oxidations of gaseous alkanes, traces of acetic acid were also detected due to partial oxidation of the MeCN solvent Stage 1: With 2-carboxypyrazine, [{VO(EtO)(EtOH)}2(1κ2O,κN:2κ2O,κN-bis(2-hydroxybenzylidene)oxalohydrazonic acid)]·2H2O, dihydrogen peroxide in water, acetonitrile, Time= 4h, T= 50 °C Stage 2: With triphenylphosphine, p= 760.051Torr , Autoclave, Overall yield = 45.3 percentChromat.

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Gupta, Samik; Kirillova, Marina V.; Guedes Da Silva, M. Fatima; Pombeiro, Armando J.L.; Applied Catalysis A: General; vol. 460-461; (2013); p. 82 - 89 View in Reaxys O O

HO O

Rx-ID: 35440694 View in Reaxys 79/804 Yield

Conditions & References

94.2 11 : Hydrogenation of BBL with a i-alumina catalyst: Continuous flow reactor setup %Chromat. 7.0 g of the NiO/alumina catalyst (Unicat, 50percentNiO/Al2O3) was placed in the reactor and covered on top with 0.9 g glass beads. The reactor was purged with nitrogen followed by a stream of 5percent H2/nitrogen at 0.3 1/min overnight at temperature of the reactor 180 °C and then 5percent H2/nitrogen was replaced by a stream of pure hydrogen at 0.3 1/min for lh. The reactor was initially heated to 260 °C, hydrogen pressure was set up to 300 psi at hydrogen flow rate of 0.40 1/min, HPLC pump was turned on and BBL was pumped at a rate of 0.04 ml/min. The experiment was run for 6 h at temperature gradient from 260 to 170 °C and samples of the reaction mixture were collected and analyzed by GC-MS analysis (in methyl acetate). The obtained results are summarized in the Table 8. With hydrogen, Time= 5.66667h, T= 200 - 247 °C , p= 15514.9Torr , Inert atmosphere Patent; PIONEER ENERGY; HENRI, John; ZYGMUNT, Jan; BERGREN, Mark; ZUBRIN, Robert; WO2013/70966; (2013); (A1) English View in Reaxys

HO OH O

Rx-ID: 35440695 View in Reaxys 80/804 Yield

Conditions & References

44.1 %Chromat., 40.5 %Chromat., 10.5 %Chromat.

9 : Hydrogenation of BBL with a i-alumina catalyst: Continuous flow reactor setup 7.0 g of the NiO/alumina catalyst (Unicat, 50percentNiO/Al2O3) was placed in the reactor and covered on top with 0.9 g glass beads. The reactor was purged with nitrogen followed by a stream of 5percent H2/nitrogen at 0.3 1/min overnight at temperature of the reactor 180 °C and then 5percent H2/nitrogen was replaced by a stream of pure hydrogen at 0.3 1/min for lh. The reactor was initially heated to 260 °C, hydrogen pressure was set up to 300 psi at hydrogen flow rate of 0.40 1/min, HPLC pump was turned on and BBL was pumped at a rate of 0.04 ml/min. The experiment was run for 6 h at temperature gradient from 260 to 170 °C and samples of the reaction mixture were collected and analyzed by GC-MS analysis (in methyl acetate). The obtained results are summarized in the Table 8. With hydrogen, Time= 5.08333h, T= 170 - 185 °C , p= 15514.9Torr , Inert atmosphere Patent; PIONEER ENERGY; HENRI, John; ZYGMUNT, Jan; BERGREN, Mark; ZUBRIN, Robert; WO2013/70966; (2013); (A1) English View in Reaxys

O O

HO OH O

Rx-ID: 35440697 View in Reaxys 81/804 Yield

Conditions & References

80 %Chro- 9 : Hydrogenation of BBL with a i-alumina catalyst: Continuous flow reactor setup mat., 13.9 7.0 g of the NiO/alumina catalyst (Unicat, 50percentNiO/Al2O3) was placed in the reactor and covered on top with %Chromat. 0.9 g glass beads. The reactor was purged with nitrogen followed by a stream of 5percent H2/nitrogen at 0.3 1/min overnight at temperature of the reactor 180 °C and then 5percent H2/nitrogen was replaced by a stream of pure hydrogen at 0.3 1/min for lh. The reactor was initially heated to 260 °C, hydrogen pressure was set up to 300 psi at hydrogen flow rate of 0.40 1/min, HPLC pump was turned on and BBL was pumped at a rate of 0.04 ml/min. The experiment was run for 6 h at temperature gradient from 260 to 170 °C and samples of the reaction mixture were collected and analyzed by GC-MS analysis (in methyl acetate). The obtained results are summarized in the Table 8. With hydrogen, Time= 5.41667h, T= 170 - 187 °C , p= 15514.9Torr , Inert atmosphere

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Patent; PIONEER ENERGY; HENRI, John; ZYGMUNT, Jan; BERGREN, Mark; ZUBRIN, Robert; WO2013/70966; (2013); (A1) English View in Reaxys Rx-ID: 35571805 View in Reaxys 82/804 Yield

Conditions & References 2.3 Photocatalytic partial oxidation of dodecane Photocatalytic reactions were performed in a continuous flow system shown in Fig. S1. The carrier gas (Ar) flew through a dodecane saturator immersed in a constant temperature silicon oil bath. A 450W Hg lamp (7825-34, Ace Glass) without cutoff filter was used as a UV–Vis source. Light intensity was 0.81W/cm2 measured by a photometer (ORIEL 70260 with 70282 head). Tubular quartz glass was used as a cooling jacket and a light window, in which cooling water was circulated. Ethanol solution of photocatalyst powders was sprayed over the glass rod on a 300°C hot plate for coating. Product compounds were analyzed by an on-line gas chromatograph (HP 6890) equipped with a DB-5 column (Agilent Technology, 125-5532) and 2 auto sampling valves for TCD and FID analysis. The products were identified with a GC (HP 6890)–MS (HP 5973) equipped with a DB-5ms column (Agilent Technology, 122-5563). With TiO2–SiO2 mixed oxide, oxygen, Time= 6h, T= 160 °C , Inert atmosphere, UV-irradiation, Catalytic behavior, Temperature, Reagent/catalyst Kim, Jae Yul; Kim, Yeon Ho; Han, Suenghoon; Choi, Sun Hee; Lee, Jae Sung; Journal of Catalysis; vol. 302; (2013); p. 58 - 66 View in Reaxys

I C

HO O

Rx-ID: 35602305 View in Reaxys 83/804 Yield

O C

O O

Rx-ID: 35602309 View in Reaxys 84/804 Yield

Conditions & References With C16H36N(1+)*Ir(1+)*2Cl(1-)*2CO, methyl iodide in water, acetic acid, Time= 5h, T= 130 °C , p= 22502.3Torr , Autoclave Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys

I C

O O

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Rx-ID: 35602310 View in Reaxys 85/804 Yield

Conditions & References With [dicarbonyldichlorodirhodium(I)], methyl iodide in water, acetic acid, Time= 5h, T= 130 °C , p= 22502.3Torr , Autoclave Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys

O C

Rx-ID: 35602311 View in Reaxys 86/804 Yield

Conditions & References With [dicarbonyldichlorodirhodium(I)], hydrogen iodide in water, acetic acid, Time= 17h, T= 180 °C , p= 22502.3Torr , Autoclave Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys With C16H36N(1+)*Ir(1+)*2Cl(1-)*2CO, hydrogen iodide in water, acetic acid, Time= 17h, T= 180 °C , p= 22502.3Torr , Autoclave Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys

O C

O O

O I

Rx-ID: 35602312 View in Reaxys 87/804 Yield

Conditions & References With [dicarbonyldichlorodirhodium(I)], hydrogen iodide in water, acetic acid, Time= 5h, T= 180 °C , p= 22502.3Torr , Autoclave Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys With C16H36N(1+)*Ir(1+)*2Cl(1-)*2CO, hydrogen iodide in water, acetic acid, Time= 5h, T= 180 °C , p= 22502.3Torr , Autoclave, Reagent/catalyst, Time Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys With hydrogen iodide in water, acetic acid, Time= 17h, T= 180 °C , Autoclave Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys

67/263

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I C

HO O

Rx-ID: 35602313 View in Reaxys 88/804 Yield

Conditions & References With C16H36N(1+)*Ir(1+)*2Cl(1-)*2CO, hydrogen iodide in water, acetic acid, Time= 5h, T= 130 °C , p= 22502.3Torr , Autoclave Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys

I C

Rx-ID: 35602314 View in Reaxys 89/804 Yield

Conditions & References With [dicarbonyldichlorodirhodium(I)], hydrogen iodide in water, acetic acid, Time= 5h, T= 130 °C , p= 22502.3Torr , Autoclave Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys With C16H36N(1+)*Ir(1+)*2Cl(1-)*2CO, hydrogen iodide in water, acetic acid, Time= 5h, T= 180 °C , p= 22502.3Torr , Autoclave, Temperature Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys

Rx-ID: 35602315 View in Reaxys 90/804 Yield

Conditions & References With C16H36N(1+)*Ir(1+)*2Cl(1-)*2CO, methyl iodide in water, acetic acid, Time= 5h, T= 180 °C , p= 22502.3Torr , Autoclave Coskun, Timur; Conifer, Christopher M.; Stevenson, Laura C.; Britovsek, George J. P.; Chemistry - A European Journal; vol. 19; nb. 21; (2013); p. 6840 - 6844 View in Reaxys

HO OH

Rx-ID: 35636128 View in Reaxys 91/804 Yield 56.5 %Chromat., 20.1 %Chro-

Conditions & References 7 : Diketene reductions in continuous flow reactor system on a Cu-Zn and nickel- alumina catalyst First 5.1 g of the CuO-ZnO catalyst (Unicat, LS-402, 5 x 2 mm) and then 1.97 g of the N1O-AI2O3 catalyst (Unicat, NH- 100, extruded) was placed in the reactor described in experiment 5 above covered on top with 1.4 g glass beads were placed in the reactor. The reactor was purged with nitrogen followed by a stream of 5percent H2/nitrogen at 0.4 1/min overnight at temperature of the reactor at 230- 240 °C and then 5percent H2/nitrogen was replaced by a

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mat., 11.5 stream of pure hydrogen at 0.4 1/min at 210 °C for 2h. The reactor was initially heated to 212 °C, hydrogen pressure %Chromat. was set up to 300 psi at hydrogen flow rate of 0.3 1/min and HPLC pump was turned on to pump diketene (GC: 91.6percent diketene, 2.9percent acetic acid, 3.9percent acetic anhydride) at a rate of 0.05 ml/min. The experiment was run for 1.7h at temperature gradient from 190 to 220 °C (catalyst temp at middle of the reactor) and samples of the reaction mixture were collected and analyzed by GC-MS analysis (in methyl acetate). GCMS qualitative analysis of products formed is shown in Table 6 and also a theoretical estimation of the calorific value of a sample mixture 5 (S5) is shown in Table 6a. 100percent of diketene was reacted, samples showed 91-96percent of product included a mixture of higher alcohols, butyrate esters and acetic acid, higher alcohols were in 34-77percent range of which 33-77percent was 1-butanol and 2-butanol. With hydrogen, Time= 1.16667h, T= 190 - 220 °C , p= 15514.9Torr , Inert atmosphere, Time Patent; PIONEER ENERGY; HENRI, John; ZYGMUNT, Jan; BERGREN, Mark; ZUBRIN, Robert; WO2013/70966; (2013); (A1) English View in Reaxys 33.3 %Chromat., 32.3 %Chromat., 17.1 %Chromat.

7 : Diketene reductions in continuous flow reactor system on a Cu-Zn and nickel- alumina catalyst First 5.1 g of the CuO-ZnO catalyst (Unicat, LS-402, 5 x 2 mm) and then 1.97 g of the N1O-AI2O3 catalyst (Unicat, NH- 100, extruded) was placed in the reactor described in experiment 5 above covered on top with 1.4 g glass beads were placed in the reactor. The reactor was purged with nitrogen followed by a stream of 5percent H2/nitrogen at 0.4 1/min overnight at temperature of the reactor at 230- 240 °C and then 5percent H2/nitrogen was replaced by a stream of pure hydrogen at 0.4 1/min at 210 °C for 2h. The reactor was initially heated to 212 °C, hydrogen pressure was set up to 300 psi at hydrogen flow rate of 0.3 1/min and HPLC pump was turned on to pump diketene (GC: 91.6percent diketene, 2.9percent acetic acid, 3.9percent acetic anhydride) at a rate of 0.05 ml/min. The experiment was run for 1.7h at temperature gradient from 190 to 220 °C (catalyst temp at middle of the reactor) and samples of the reaction mixture were collected and analyzed by GC-MS analysis (in methyl acetate). GCMS qualitative analysis of products formed is shown in Table 6 and also a theoretical estimation of the calorific value of a sample mixture 5 (S5) is shown in Table 6a. 100percent of diketene was reacted, samples showed 91-96percent of product included a mixture of higher alcohols, butyrate esters and acetic acid, higher alcohols were in 34-77percent range of which 33-77percent was 1-butanol and 2-butanol. With hydrogen, Time= 1.68333h, T= 190 - 220 °C , p= 15514.9Torr , Inert atmosphere Patent; PIONEER ENERGY; HENRI, John; ZYGMUNT, Jan; BERGREN, Mark; ZUBRIN, Robert; WO2013/70966; (2013); (A1) English View in Reaxys

40.2 %Chromat., 19.2 %Chromat., 13.4 %Chromat.

6 : Diketene reductions in continuous flow reactor system on a nickel-alumina catalyst 5.3 g of the N1O-AI2O3 catalyst (Unicat, NH-100, extruded) was placed in the reactor described in experiment 5 above and covered on top with 1.3 g glass beads. The reactor was purged with nitrogen followed by a stream of 5percent H2/nitrogen at 0.4 1/min overnight at temperature of the reactor at 190 C and then 5percent E^/nitrogen was replaced by a stream of pure hydrogen at 0.4 1/min at 190-195 C for 2h. The reactor was initially heated to 193 C, hydrogen pressure was set up to 300 psi at hydrogen flow rate of 0.3 1/min and HPLC pump was turned on to pump diketene (GC: 95.1percent diketene, 3.5percent acetic acid, 0.7percent acetic anhydride) at a rate of 0.05 ml/ min. The experiment was run for 1.5h at temperature gradient from 195 to 240 °C (catalyst temp at middle of the reactor) and samples of the reaction mixture were collected and analyzed by GC-MS analysis (in methyl acetate). GCMS qualitative analysis of products formed is shown in Table 5 and also a theoretical estimation of the calorific value of a sample mixture 3 (S3) is shown in Table 5 a. 100percent of diketene was reacted with product showing 41-51percent higher alcohols of which 35-43percent was 1-butanol and 2-butanol. The mixture was observed to also contain other products including butyrate esters, acetic acid which along with higher alcohols were about 88percent. With hydrogen, Time= 0.8h, T= 195 - 240 °C , p= 15514.9Torr , Inert atmosphere, Time Patent; PIONEER ENERGY; HENRI, John; ZYGMUNT, Jan; BERGREN, Mark; ZUBRIN, Robert; WO2013/70966; (2013); (A1) English View in Reaxys

OH OH

HO O

Rx-ID: 36212104 View in Reaxys 92/804

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Yield

Conditions & References

60 %

With tert.-butylhydroperoxide, potassium tert-butylate in water, Time= 8h, T= 80 °C Shaikh, Tanveer Mahammadali; Hong, Fung-E; Tetrahedron; vol. 69; nb. 42; (2013); p. 8929 - 8935 View in Reaxys

OH O

Rx-ID: 36212105 View in Reaxys 93/804 Yield

Conditions & References

64 %

With tert.-butylhydroperoxide, potassium tert-butylate in water, Time= 8h, T= 80 °C Shaikh, Tanveer Mahammadali; Hong, Fung-E; Tetrahedron; vol. 69; nb. 42; (2013); p. 8929 - 8935 View in Reaxys O

OH O

HO OH

Rx-ID: 36543367 View in Reaxys 94/804 Yield

Conditions & References With hydrogen in water, Time= 50h, T= 160 °C , p= 112511Torr , Inert atmosphere, High pressure, Sonication, Reagent/catalyst Tapin, Benoit; Epron, Florence; Especel, Catherine; Ly, Bao Khanh; Pinel, Catherine; Besson, Michele; ACS Catalysis; vol. 3; nb. 10; (2013); p. 2327 - 2335 View in Reaxys

HO OH O

Rx-ID: 38797608 View in Reaxys 95/804 Yield

Conditions & References

63 %

O O

HO O

Rx-ID: 8775930 View in Reaxys 96/804 Yield

Conditions & References With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, lipase from Bacillus thermocatenulanatus in water, T= 40 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, lipase from Ophiostoma piliferum in water, T= 25 °C , pH= 7.20, Enzyme kinetics

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Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, esterase from Pseudomonas fluorescens in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, esterase from Streptomyces diastatochromogenes in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With recombinant Escherichia coli esterase YbfF W235I mutant in aq. buffer, T= 30 °C , pH= 7.5, Enzymatic reaction, Kinetics, Concentration, Reagent/catalyst Godinho, Luis F.; Reis, Carlos R.; Van Merkerk, Ronald; Poelarends, Gerrit J.; Quax, Wim J.; Advanced Synthesis and Catalysis; vol. 354; nb. 16; (2012); p. 3009 - 3015 View in Reaxys

O O

Rx-ID: 32781037 View in Reaxys 97/804 Yield

Conditions & References With potassium chloride, water, sodium chloride, calcium chloride, magnesium chloride, 2-[4-(2-hydroxyethyl)-1-piperazinyl] ethanesulfonic acid in methanol, pH= 7.2, UV-irradiation, Kinetics Soares, Ana M. S.; Piloto, Ana M.; Hungerford, Graham; Costa, Susana P. G.; Goncalves, M. Sameiro T.; European Journal of Organic Chemistry; nb. 5; (2012); p. 922 - 930 View in Reaxys

O O

Rx-ID: 32781038 View in Reaxys 98/804 Yield

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O N

O O

Rx-ID: 32781040 View in Reaxys 99/804 Yield

Rx-ID: 32781041 View in Reaxys 100/804 Yield

O HO

N O

Rx-ID: 32781043 View in Reaxys 101/804 Yield

Rx-ID: 33663547 View in Reaxys 102/804 Yield

Conditions & References With methanol, oxygen, chlorine, T= 21.84 °C , p= 800Torr , Photolysis Hasson, Alam S.; Tyndall, Geoffrey S.; Orlando, John J.; Singh, Sukhdeep; Hernandez, Samuel Q.; Campbell, Sean; Ibarra, Yesenia; Journal of Physical Chemistry A; vol. 116; nb. 24; (2012); p. 6264 - 6281 View in Reaxys

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O O

Rx-ID: 33716500 View in Reaxys 103/804 Yield

Conditions & References With acetyl esterase from thermotoga maritima, water in acetonitrile, Time= 0.0666667h, T= 25 °C , aq. phosphate buffer, Enzymatic reaction, Kinetics, Concentration Hedge, Matthew K.; Gehring, Alexandra M.; Adkins, Chinessa T.; Weston, Leigh A.; Lavis, Luke D.; Johnson, R. Jeremy; Biochimica et Biophysica Acta - Proteins and Proteomics; vol. 1824; nb. 9; (2012); p. 1024 - 1030 View in Reaxys

HO O

Rx-ID: 34416342 View in Reaxys 104/804 Yield

Conditions & References With recombinant Escherichia coli esterase YbfF W235I mutant in aq. buffer, T= 30 °C , pH= 7.5, Enzymatic reaction Godinho, Luis F.; Reis, Carlos R.; Van Merkerk, Ronald; Poelarends, Gerrit J.; Quax, Wim J.; Advanced Synthesis and Catalysis; vol. 354; nb. 16; (2012); p. 3009 - 3015 View in Reaxys

NH 2

O O

NH 2

Rx-ID: 34485739 View in Reaxys 105/804 Yield

Conditions & References With tert -butyl hydrogen peroxide, zinc dibromide in pyridine, water, Time= 16h, T= 80 °C Wu, Xiao-Feng; Bheeter, Charles Beromeo; Neumann, Helfried; Dixneuf, Pierre H.; Beller, Matthias; Chemical Communications; vol. 48; nb. 100; (2012); p. 12237 - 12239 View in Reaxys

O O

Rx-ID: 215553 View in Reaxys 106/804 Yield 70 %

Conditions & References With anhydrous lithium nitrate in water, acetonitrile, T= 25 °C , anodic oxidation Shono, Tatsuya; Yamamoto, Yoshinari; Takigawa, Katsuya; Maekawa, Hirofumi; Ishifune, Manabu; Kashimura, Shigenori; Chemistry Letters; nb. 6; (1994); p. 1045 - 1048 View in Reaxys

66 %

With nitric acid in water, Time= 2h, T= 50 °C Svetlakov; Nikitin; Nikolaeva; Russian Journal of Organic Chemistry; vol. 43; nb. 5; (2007); p. 771 - 772 View in Reaxys

54 %

With TS-1 (titanium silicate), dihydrogen peroxide Sasidharan; Suresh; Sudalai; Tetrahedron Letters; vol. 36; nb. 49; (1995); p. 9071 - 9072 View in Reaxys T= 70 - 75 °C , Irradiation.im diffusen Licht Clover; Journal of the American Chemical Society; vol. 46; (1924); p. 423

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View in Reaxys Irradiation.mit Sonnenlicht bei gewoehnlicher Temperatur Clover; Journal of the American Chemical Society; vol. 46; (1924); p. 423 View in Reaxys With anhydrous lithium nitrate in water, acetonitrile, T= 25 °C , anodic oxiadtion; other ethers Shono, Tatsuya; Yamamoto, Yoshinari; Takigawa, Katsuya; Maekawa, Hirofumi; Ishifune, Manabu; Kashimura, Shigenori; Chemistry Letters; nb. 6; (1994); p. 1045 - 1048 View in Reaxys With dihydrogen peroxide in water, Time= 12h, T= 69.84 °C Sasidharan, Manickam; Bhaumik, Asim; Journal of Molecular Catalysis A: Chemical; vol. 338; nb. 1-2; (2011); p. 105 - 110 View in Reaxys

HO O

Rx-ID: 8746562 View in Reaxys 107/804 Yield

Conditions & References

75 %, 23 %

With octanoic acid, dihydrogen peroxide in water, Time= 5h, T= 50 °C , Ionic liquid, Enzymatic reaction, BaeyerVilliger oxidation Kotlewska, Aleksandra J.; Van Rantwijk, Fred; Sheldon, Roger A.; Arends, Isabel W.C.E.; Green Chemistry; vol. 13; nb. 8; (2011); p. 2154 - 2160 View in Reaxys With anhydrous butyl ether, bis[3,5-bis(trifluoromethyl)diphenyl] diselenide in 2,2,2-trifluoroethanol, Time= 24h, T= 20 °C , Baeyer-Villiger oxidation Ten Brink; Vis; Arends; Sheldon; Journal of Organic Chemistry; vol. 66; nb. 7; (2001); p. 2429 - 2433 View in Reaxys

O O

H HO

O O

Rx-ID: 30189667 View in Reaxys 108/804 Yield

Conditions & References With lipase from Candida rugosa-conjugated magnetic nanobead, Time= 24h, T= 30 °C , pH= 7.4, aq. phosphate buffer, optical yield given as percent ee Sim, Yong Kyun; Jung, Suhyun; Lim, Jung Yun; Kim, Juhyun; Kim, Seong-Ho; Song, Bong Keun; Kim, Bum Tae; Lee, Hyuk; Park, Seongsoon; Tetrahedron Letters; vol. 52; nb. 9; (2011); p. 1041 - 1043 View in Reaxys

O O

H HO

HO O

Rx-ID: 30189668 View in Reaxys 109/804

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Yield

Conditions & References With lipase from Burkholderia cepacia (free form) -conjugated magnetic nanobead, Time= 24h, T= 30 °C , pH= 7.4, aq. phosphate buffer, optical yield given as percent ee Sim, Yong Kyun; Jung, Suhyun; Lim, Jung Yun; Kim, Juhyun; Kim, Seong-Ho; Song, Bong Keun; Kim, Bum Tae; Lee, Hyuk; Park, Seongsoon; Tetrahedron Letters; vol. 52; nb. 9; (2011); p. 1041 - 1043 View in Reaxys

O O

Rx-ID: 30189669 View in Reaxys 110/804 Yield

Conditions & References With CAL-B-conjugated magnetic nanobead, Time= 24h, T= 30 °C , pH= 7.4, aq. phosphate buffer, optical yield given as percent ee Sim, Yong Kyun; Jung, Suhyun; Lim, Jung Yun; Kim, Juhyun; Kim, Seong-Ho; Song, Bong Keun; Kim, Bum Tae; Lee, Hyuk; Park, Seongsoon; Tetrahedron Letters; vol. 52; nb. 9; (2011); p. 1041 - 1043 View in Reaxys O

O S

HO O

Rx-ID: 30646696 View in Reaxys 111/804 Yield

Conditions & References

67 %

Stage 1: With potassium hexamethylsilazane in tetrahydrofuran, toluene, Time= 0.5h, T= -78 °C , Inert atmosphere Stage 2: With oxygen in tetrahydrofuran, toluene, T= -78 °C Stage 3: With hydrogenchloride in water, T= 20 °C , pH= 1.2 Bonaparte, Amy C.; Betush, Matthew P.; Panseri, Bettina M.; Mastarone, Daniel J.; Murphy, Ryan K.; Murphree, S. Shaun; Organic Letters; vol. 13; nb. 6; (2011); p. 1447 - 1449 View in Reaxys

O O

Rx-ID: 30786670 View in Reaxys 112/804 Yield

Conditions & References

97 %Chro- With dichloro bis(acetonitrile) palladium(II), tris(acetonitrile)(η5-2,4-cyclopentadien-1-yl)ruthenium(1+) hexafluoromat., 81 phosphate(1-), diethylene glycol dimethyl ether, 1,6-bis-(diphenylphosphino)-hexane, water in ethylene glycol di%Chromat. methyl ether, dichloromethane, Time= 1.33333h, T= 20 - 85 °C , Inert atmosphere Nakamura, Asami; Hamasaki, Akiyuki; Goto, Sachihiko; Utsunomiya, Masaru; Tokunaga, Makoto; Advanced Synthesis and Catalysis; vol. 353; nb. 6; (2011); p. 973 - 984 View in Reaxys

O O O

O HO O

NH O

N O

N H

Rx-ID: 31018639 View in Reaxys 113/804

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Yield

Conditions & References With 4-t-butyl vinyl benzene, oxygen, hydrazine hydrate in acetonitrile, T= 30 °C Imada, Yasushi; Iida, Hiroki; Kitagawa, Takahiro; Naota, Takeshi; Chemistry - A European Journal; vol. 17; nb. 21; (2011); p. 5908 - 5920 View in Reaxys

HO O

Rx-ID: 31130831 View in Reaxys 114/804 Yield 52 %

Conditions & References Stage 1: With tert.-butylhydroperoxide, FeCl3*6H2O, sodium hydroxide in water, Time= 14h, T= 80 °C Stage 2: With hydrogenchloride in water, T= 20 °C Shaikh, Tanveer Mahamadali; Hong, Fung-E; Advanced Synthesis and Catalysis; vol. 353; nb. 9; (2011); p. 1491 1496 View in Reaxys Rx-ID: 31959212 View in Reaxys 115/804

Yield

Conditions & References With 2,2'-azo-bisisobutyronitrile, oxygen, Time= 2h, T= 90 °C , p= 9000.9Torr , Autoclave Lloyd, Rhys; Jenkins, Robert L.; Piccinini, Marco; He, Qian; Kiely, Christopher J.; Carley, Albert F.; Golunski, Stanislaw E.; Bethell, Donald; Bartley, Jonathan K.; Hutchings, Graham J.; Journal of Catalysis; vol. 283; nb. 2; (2011); p. 161 - 167 View in Reaxys Rx-ID: 31990435 View in Reaxys 116/804

Yield

Conditions & References 3 :Direct aqueous phase reforming (APR) experiments were conducted in 100-ml stirred reactors with draft-tube gasinduction impeller (Parr Series 4590). Reaction tests for direct bio-based feedstock aqueous phase reforming (APR) entailed filling the reactor with 60-grams of solvent (deionized water, or a mixture of DI water and isopropanol (IPA), and 3-3.5 grams of bio-based feedstock comprising biomass (bagasse, or pine sawdust)). One (1) gram of acetic acid was optionally charged to facilitate biomass hydrolysis.[0098] Bagasse was milled via a 1-mm grate. Dry, debarked Loblolly pine was ground via blender (Thomas Scientific of Swedesboro, NJ) and sieved to less than 30 mesh. Dry solids fraction was determined by vacuum drying at 80 °C to 82 °C. One gram of aqueous phase reforming catalyst (reduced 5percent Pt/C catalyst at 50percent moisture, or powdered 1.9percent Pt/A1203) was charged to the reactor, which was charged with 4200 kPa of hydrogen or nitrogen. To minimize degradation of hydrolysate to heavy ends, each reactor was typically heated with a staged temperature sequence of one hour at, 160 °C, 190 °C, 225 °C, and finally 250 °C, before leaving overnight at the final setpoint.[0099] Comparison tests were also conducted with glucose or sorbitol fed directly to the reaction in place of biomass, to simulate and quantify conversion of model hydrolysate to APR intermediates. Glucose is one of the sugars readily leached from biomass in hot water, while sorbitol is readily formed via hydrogenation of glucose, where platinum or other catalysts capable of hydrogenation are present.[00100] A batch reaction time of 20 hours under these conditions corresponds to a weight hourly space velocity (g-feed/g-catalyst/h) of about 3, for a comparable continuous flow reactor. A 0.5-micron sintered metal filter attached to a dip tube allowed liquid samples to be taken throughout the course of reaction, without loss of biomass or catalyst. Samples were analyzed by an HPLC method based on combined size and ion exclusionchromatography, to determine unreacted sorbitol, and amount of C3 and smaller polyols formed: glycerol (Gly), ethylene glycol (EG), and 1,2-propylene glycol (PG). Additional GC analysis via a moderate polarity DB-5 column were conducted to assess formation of C6 and lighter oxygenates (e.g., ketones, aldehydes, alcohols), as well as alkane and alkene products. A separate GC equipped with thermal conductivity and flame ionization (FID) detectors for refinery gas analysis, were used for detection of H2, C02, and light alkanes C1-C5. GC-mass spec was used to characterize select APR reaction product mixtures. Examples 1-3[00101] Batch APR reactions with sugar cane bagasse as biomass feed, and with a comparison of 25percent sorbitol as feed, were performed as described above. 1.7percent acetic acid was added to simulate catalysis of hydrolysis by recycle acid. Products formed from this concentration of acetic acid were subtracted from total product formation, to calculate the net production of liquid fuels from bagasse. This result shown in Table 1 shows the critical importance of concerted APR reaction with hydrolysis of biomass. In the absence of concerted aqueous phase reforming, the hydrolysate undergoes irreversible degradation (presumably to heavy ends), and cannot be reverted to liquid fuels upon subsequent APR and condensation. Converted reac-

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tion may be effected by direct inclusion of APR catalyst in the hydrolysis reactor, or via a pump around loop to recirculate liquid between a biomass contactor, and an APR catalytic reactor. Table 1: Direct APR of Biomass With platinum on carbon in water, Time= 3h, Direct aqueous phase reforming Patent; SHELL OIL COMPANY; SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.; CHHEDA, Juben Nemchand; ORTIZ-SOTO, Lorna Beatriz; POWELL, Joseph Broun; WO2011/143392; (2011); (A1) English View in Reaxys

O O

H O

O O

HO O

Rx-ID: 32257446 View in Reaxys 117/804 Yield

Conditions & References Stage 1: With pancreatin, deoxycholic acid sodium salt, cholic acid sodium salt, sodium chloride, calcium chloride, Time= 1h, T= 37 °C , pH= 6.5 - 7.2, Trizma-maleate buffer Stage 2: With hydrogenchloride in water Martin, Diana; Moran-Valero, Maria I.; Senorans, Francisco J.; Reglero, Guillermo; Torres, Carlos F.; Lipids; vol. 46; nb. 3; (2011); p. 277 - 285 View in Reaxys

Rx-ID: 32412954 View in Reaxys 118/804 Yield

Conditions & References With methyl(trifluoromethyl)dioxirane in dichloromethane, Time= 8h, T= -15 °C , Darkness Mello, Rossella; Martinez-Ferrer, Jaime; Alcalde-Aragones, Ana; Varea, Teresa; Acerete, Rafael; GonzalezNunez, Maria Elena; Asensio, Gregorio; Journal of Organic Chemistry; vol. 76; nb. 24; (2011); p. 10129 - 10139 View in Reaxys

Si O

Rx-ID: 32412957 View in Reaxys 119/804 Yield

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O O

Rx-ID: 32412959 View in Reaxys 120/804 Yield

Si O

Rx-ID: 32412960 View in Reaxys 121/804 Yield

Rx-ID: 32978390 View in Reaxys 122/804 Yield

Conditions & References With ZrO2 (7)-FeOX in water, Time= 2h, T= 349.84 °C , p= 760.051Torr , Inert atmosphere Yoshikawa, Takuya; Tago, Teruoki; Nakamura, Ayaka; Konaka, Aya; Mukaida, Mitsushi; Masuda, Takao; Research on Chemical Intermediates; vol. 37; nb. 9; (2011); p. 1247 - 1256 View in Reaxys

H 2N

H N

Rx-ID: 1356894 View in Reaxys 123/804 Yield 87 %

Conditions & References With water, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in chloroform, Time= 1h, T= 20 °C Takale, Balaram S.; Telvekar, Vikas N.; Chemistry Letters; vol. 39; nb. 6; (2010); p. 546 - 547 View in Reaxys With sulfuric acid, T= 70 - 80 °C , Equilibrium constant, Kinetics Grekov,A.P. et al.; Journal of Organic Chemistry USSR (English Translation); vol. 6; nb. 1; (1970); p. 93 - 96; Zhurnal Organicheskoi Khimii; vol. 6; nb. 1; (1970); p. 94 - 97 View in Reaxys With sulfuric acid in water, T= 55 °C , Mechanism, Rate constant Cox, Robin A.; Yates, Keith; Canadian Journal of Chemistry; vol. 62; (1984); p. 1613 - 1617 View in Reaxys With perchloric acid, water, potassium hexacyanoferrate(III), T= 30 °C , Ea, ΔH(excit.), ΔG(excit.), ΔS(excit.), also in the presence of NaClO4, NaNO3, NaCl, KCl or LiCl, also in methanol, effect of substrate, K4Fe(CN)6 and HClO4 concentrations, Rate constant, Thermodynamic data, Mechanism

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Hongekar; Patil; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 37; nb. 6; (1998); p. 493 - 497 View in Reaxys

HO O

Rx-ID: 8748641 View in Reaxys 124/804 Yield

Conditions & References With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, esterase from Streptomyces diastatochromogenes in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, esterase from Pseudomonas fluorescens in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, lipase from Ophiostoma piliferum in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, lipase from Bacillus thermocatenulanatus in water, T= 40 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys With bovine pancreatic bile-salt-activated lipase, water, tris(hydroxymethyl)methylamine hydrochloride, sodium chloride, T= 25 °C , pH= 7, Enzymatic reaction, Kinetics, Reagent/catalyst Chahinian, Henri; Fantini, Jacques; Garmy, Nicolas; Manco, Giuseppe; Sarda, Louis; Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids; vol. 1801; nb. 11; (2010); p. 1195 - 1204 View in Reaxys

O O

Rx-ID: 29763557 View in Reaxys 125/804 Yield

Conditions & References

61 %Chro- With water, difluoro[4-(trifluoromethyl)phenyl]-λ(3)-bromane in dichloromethane, Time= 1h, T= 0 °C , Inert atmosmat., 14 phere, Baeyer-Villiger type oxidation %Chromat. Ochiai, Masahito; Yoshimura, Akira; Miyamoto, Kazunori; Hayashi, Satoko; Nakanishi, Waro; Journal of the American Chemical Society; vol. 132; nb. 27; (2010); p. 9236 - 9239 View in Reaxys

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O HO

HO O

Rx-ID: 29783628 View in Reaxys 126/804 Yield

Conditions & References

54 %

With hydrogen in 1,4-dioxane, Time= 4h, T= 260 °C , p= 45004.5Torr , Inert atmosphere Hong, Ung Gi; Hwang, Sunhwan; Seo, Jeong Gil; Yi, Jongheop; Song, In Kyu; Catalysis Letters; vol. 138; nb. 1-2; (2010); p. 28 - 33 View in Reaxys

HO O

Rx-ID: 29985173 View in Reaxys 127/804 Yield

Conditions & References With water, oxygen, Titanium(IV) oxide, UV-irradiation Wen, Bo; Li, Yue; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Chemistry - A European Journal; vol. 16; nb. 39; (2010); p. 11859 - 11866 View in Reaxys

Rx-ID: 30091250 View in Reaxys 128/804 Yield

Conditions & References With Candida antarctica lipase B, water, Enzymatic reaction Larsen, Marianne Wittrup; Zielinska, Dorota F.; Martinelle, Mats; Hidalgo, Aurelio; Jensen, Lars Juhl; Bornscheuer, Uwe T.; Hult, Karl; ChemBioChem; vol. 11; nb. 6; (2010); p. 796 - 801 View in Reaxys

HO O

Rx-ID: 28825291 View in Reaxys 129/804 Yield

Conditions & References

85 %

Stage 1: With sodium tetrahydroborate in dimethyl sulfoxide, T= 20 °C Stage 2: With hydrogenchloride, water in dimethyl sulfoxide, Time= 0.5h, chemoselective reaction Pawar, Bharati V.; Lokhande, Pradeep D.; Synthetic Communications; vol. 39; nb. 14; (2009); p. 2445 - 2453 View in Reaxys

H H

(v5)

H P

–

B– PH

Rx-ID: 28922803 View in Reaxys 130/804 Yield

Conditions & References T= 57.84 °C , Gas phase, Equilibrium constant Hurtado, Marcela; Yanez, Manuel; Herrero, Rebeca; Guerrero, Andres; Juan Z. Davalos; Jose-Luis, M. Abboud; Khater, Brahim; Guillemin, Jean-Claude; Chemistry - A European Journal; vol. 15; nb. 18; (2009); p. 4622 4629 View in Reaxys

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O OH

HO O O

O O

OH OH

OH O

OH HO

O HO

OH OH

O O

OH O

OH OH

Rx-ID: 29243720 View in Reaxys 131/804 Yield

Conditions & References With water, sodium hydroxide in ethanol, Time= 1h, Reflux Leon-Rivera, Ismael; Miron-Lopez, Gumersindo; Estrada-Soto, Samuel; Aguirre-Crespo, Francisco; Gutierrez, Maria del Carmen; Molina-Salinas, Gloria Maria; Hurtado, Gerardo; Navarrete-Vazquez, Gabriel; Montiel, Elizur; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 16; (2009); p. 4652 - 4656 View in Reaxys

O O

Rx-ID: 27788084 View in Reaxys 132/804 Yield

Conditions & References 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of

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enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, M. smegmatis perhydrolase, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, Reactivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys O O

O O

HO O

Rx-ID: 27788097 View in Reaxys 133/804 Yield

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SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, MsAcT perhydrolase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti

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With water, dihydrogen peroxide, Pseudomonas sp. lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, cholesterol esterase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay

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solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, rhizopus oryzae lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices,

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SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Pseudomonas cepacia lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti

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With water, dihydrogen peroxide, pseudomonas fluorescens lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, cutinase in hexane, Time= 0.0666667 - 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay

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solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Mucor miehei lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices,

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SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Candida antarctica Type B lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti

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With water, dihydrogen peroxide, AchE enzyme in hexane, Time= 0.0666667 - 0.5h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Alciligenes sp. lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay

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solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Candida antarctica type A lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices,

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SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Candida rugosa enzyme in hexane, Time= 0.0666667 - 0.5h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti

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With water, dihydrogen peroxide, Chirazyme L2 - CalB enzyme in hexane, Time= 0.0666667 - 0.5h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Chirazyme L5 - CalA enzyme in hexane, Time= 0.0666667 - 0.5h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the en-

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zyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, ESB120 enzyme in hexane, Time= 0.0666667 - 0.5h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the

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absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Lipolase enzyme in hexane, Time= 0.0666667 - 0.5h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has ac-

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tivity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, M. smegmatis perhydrolase, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, Polyester fabric, Reactivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, MpAcT enzyme in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the

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substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Mucor meihei enzyme in hexane, Time= 0.0666667 - 0.5h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the en-

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zyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, novo 525L lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared

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to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, porcine pancreas enzyme in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys 2 :Determination of Perhydrolysis (OPD Assay)The perhydrolytic activity assay described below was used to determine the amount of peracid formed in the reaction. In these assays, the solution comprised 50 mM potassium phosphate pH 7.5, 10 mM ester substrate, 29 mM hydrogen peroxide, 20 mM potassium chloride, and 10 mM O-phenylenediamine.When using water insoluble ester as the acyl donor, an ester adsorbed fabric swatch was used as the substrate, prepared as described above ("Preparation of Substrate").Perhydrolytic activity was measured by monitoring the absorbance increase at 458 nm of oxidized O-phenylenediamine (OPD) by peracid generated with the enzyme. The perhydrolytic activity assay solution was prepared in the same manner as the hydrolytic activity assay solution, except that OPD was added to the assay solution to a final concentration of 10 mM. The OPD solution was prepared immediately before conducting the assay by dissolving 72 mg OPD (Sigma-Aldrich, dihydrochloride) in 19.94 mL of the same buffer and the pH was adjusted by slowly adding 60 μL of 13.5 M potassium hydroxide. The pH was measured and if needed, small quantities of potassium hydroxide were added to return the pH to the original pH of the buffer. Then, 495 μL of this OPD solution were added with the other assay components to a final assay volume of 0.990 mL. An assay quenching solution was also prepared by dissolving 36 mg OPD in 20 mL 100 mM citric acid and 70percent ethanol.The assay was typically conducted at 25° C. The assay was started by pipetting 100 μL of assay solution before the addition of the enzyme into 200 μL of quenching solution to determine the amount of perhydrolytic components and background absorbance in the assay solution at time 0. Then, 10 μL of enzyme were added to the assay solution to a desired final concentration which produced approximately 10 nanomoles of peracid per minute. A timer was started and 100 μL aliquots were taken from the assay solution and added to 200 μL of quenching solution at various times, typically 2, 5, 10, 15, 25, 40, and 60 minutes, after adding the enzyme. The quenched assay solutions were incubated for 30 minutes to allow any remaining peracid to oxidize the OPD. Then, 100 μL of each quenched assay solution was transferred to a 96-well microtiter plate (Costar) and the absorbance of the solution was measured at 458 nm by a spectrophotometric plate reader (Molecular Devices, SpectraMAX 250). The amount of peracid in each quenched sample was calculated using a standard curve generated under the above conditions with peracetic acid at varying concentrations in the assay solution (without enzyme).Perhydrolysis/Hydrolysis Ratio:Perhydrolysis/Hydrolysis ratio=Perhydrolysis measured in the Perhydrolysis assay/(Total acid detected in the hydrolysis assay-Perhydrolysis measured in the perhydrolysis assay)The results of these experiments are provided in FIGS. 7, 10 and FIG. 11. FIG. 7 provides a graph which shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 40 minutes. FIG. 10 shows the ratio of perbutyric acid to butyric acid generated by various enzymes from 10 mM tributyrin and 29 mM hydrogen peroxide in 4, 10, and 30 minutes. FIG. 11 shows the ratio of peracetic acid to acetic acid generated by various enzymes from 10 mM triacetin and 29 mM hydrogen peroxide in 4 and 10 minutes. The results obtained in these experiments indicated that M. smegmatis perhydrolase homologues exhibited a ratio above 1 in the OPD/GC assays described above, while other classes of enzymes exhibited ratios significantly below 1.Table 2-1 provides data showing the perhydrolysis activity of various homologues described herein on triacetin, as compared to the wild-type M. smegmatis perhydrolase. The results provided in Table 2-2 indicate that the perhydrolase has activity over a broad range of substrates. In addition to the results provided in these Tables, FIGS. 8 and 9 provide data showing that the perhydrolase of the present invention has broad pH and temperature range activiti With water, dihydrogen peroxide, Thermomyces lanuginosas lipase in hexane, Time= 0.666667h, pH= 7.5, Potassium phosphate 50 mM, Potassium chloride 20 mM, polyester fabric, Product distribution / selectivity Patent; Amin, Neelam S.; Boston, Matthew G.; Bott, Richard R.; Cervin, Marguerite A.; Concar, Edward M.; Gustwiller, Marc E.; Jones, Brain E.; Liebeton, Klaus; Miracle, Gregory S.; Oh, Hiroshi; Poulose, Ayrookaran J.; Ramer, Sandra W.; Scheibel, Jeffrey J.; Weyler, Walter; Whited, Gregory M.; US2008/145353; (2008); (A1) English View in Reaxys

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Rx-ID: 27844293 View in Reaxys 134/804 Yield

Conditions & References

29.8 2 %ChroPatent; INSTITUTO SUPERIOR TECNICO; WO2008/88234; (2008); (A1) English mat., 4.6 %Chromat. View in Reaxys

Rx-ID: 27935352 View in Reaxys 135/804 Yield

Conditions & References With hydroxylamine, Na3[Fe(CN)5NH3]*3H2O in various solvent(s), T= 100 °C , pH= 9.3 Gaviglio, Carina; Doctorovich, Fabio; Journal of Organic Chemistry; vol. 73; nb. 14; (2008); p. 5379 - 5384 View in Reaxys

Rx-ID: 27985375 View in Reaxys 136/804 Yield

Conditions & References

48 %

With tetraethylammonium chloride, silver, magnesium in acetonitrile, T= 0 °C , p= 760.051Torr , Electrolysis Niu, Dong-Fang; Xiao, Li-Ping; Zhang, Ai-Jian; Zhang, Gui-Rong; Tan, Qi-Yun; Lu, Jia-Xing; Tetrahedron; vol. 64; nb. 46; (2008); p. 10517 - 10520 View in Reaxys

O HO

Rx-ID: 28331332 View in Reaxys 137/804 Yield

Conditions & References With Au-TiO2 nanoparticles, hydrogen in 1,4-dioxane, T= 250 °C , p= 45004.5Torr , Inert atmosphere, Reactivity, Pressure Budroni, Gerolamo; Corma, Avelino; Journal of Catalysis; vol. 257; nb. 2; (2008); p. 403 - 408 View in Reaxys

O O

HO O

Rx-ID: 28476403 View in Reaxys 138/804 Yield

Conditions & References With Rh on carbon, hydrogen in benzene Mohrig, Jerry R.; Alberg, David G.; Cartwright, Craig H.; Pflum, Mary Kay H.; Aldrich, Jeffrey S.; Anderson, J. Kyle; Anderson, Shelby R.; Fimmen, Ryan L.; Snover, Amy K.; Organic and Biomolecular Chemistry; vol. 6; nb. 9; (2008); p. 1641 - 1646 View in Reaxys

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Rx-ID: 197390 View in Reaxys 139/804 Yield

Conditions & References With Pd-BaSO4, ethanol, Hydrogenation Paal; Schiedewitz; Chemische Berichte; vol. 63; (1930); p. 768 View in Reaxys

50 % Spectr.

With supercritical carbon dioxide, hydrogen, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate in water, Time= 1h, T= 56 °C , p= 22502.3Torr Burgemeister, Katja; Francio, Giancarlo; Gego, Volker H.; Greiner, Lasse; Hugl, Herbert; Leitner, Walter; Chemistry - A European Journal; vol. 13; nb. 10; (2007); p. 2798 - 2804 View in Reaxys O HO O

Rx-ID: 1832373 View in Reaxys 140/804 Yield 88 %

Conditions & References With sodium hypochlorite in acetonitrile, Time= 1h, T= 20 °C Khurana; Sharma; Gogia; Kandpal; Organic Preparations and Procedures International; vol. 39; nb. 2; (2007); p. 185 - 189 View in Reaxys

With dihydrogen peroxide, tris(cetyl)pyridinium 12-tungstophosphate in chloroform, Time= 24h, Heating Ishii, Yasutaka; Sakata, Yasuyuki; Journal of Organic Chemistry; vol. 55; nb. 21; (1990); p. 5545 - 5547 View in Reaxys

HO O

Rx-ID: 10720263 View in Reaxys 141/804 Yield

Conditions & References 2 :EXAMPLE 2 This example illustrates the hydroformylation of propylene obtainable from oxygenates and the impact of various impurities therein. It was found that methyl mercaptan when present in propylene, impairs rhodium catalysed hydroformylation. Beside the reaction rate reduction, it was found that such sulphur components react in the process with formation of higher boiling sulphur species. Surprisingly it was found that dimethyl ether has marginal or no effect on the reaction rate and these components were found unchanged in the product after reaction. More particularly, it was found that: Methyl mercaptan, when present in a S/Rh molar ratio of 20/1, decreased the hydroformylation rate of propylene in a low pressure Rh/triphenyl phospine (TPP) hydroformylation kinetic experiment by 90percent compared to a reference experiment without methyl mercaptan. Dimethyl ether (DME), when present in a DME/Rh molar ratio of 20/1 and 80/1 showed no effect on the hydroformylation rate of propylene compared to the reference experiments without DME. This therefore illustrates the benefits derived from the use of feeds low in sulphur such as those obtained by the conversion of oxygenates to olefins. Hydroformylation kinetic experiments were carried out in a standard half liter zipperclave from Autoclave Engineers. Mixing occurred with an air driven stirrer with speed controlled at 2000 revolutions per minute. The mixer had a six bladed impeller that guaranteed a strong mixing between the gas and the liquid phase. Baffles inside the reactor prevented vortex formation and created back mixing. The reaction temperature was controlled at 110° C.+/-1° C. Pressure was controlled at 1000 kpag+/-10 kPa (10 barg+/-0.1 bar). Synthesis gas (48percent H2 and 52percent CO) was delivered from a calibrated high pressure storage cylinder equipped with a pressure transmitter allowing pressure reading at 1 kPa (0.01 bar) accuracy. Each experiment started with a catalyst solution of the following composition: Triphenyl phosphine (TPP)=19.84 g Tetraglyme (solvent)=191.2 g Rhodium=0.00576 g The rhodium was dosed using rhodium carbonyl acetylacetonate as catalyst precursor. The catalyst solution contained 27 wtppm rhodium. The catalyst solution was transferred into the reactor and the reactor was purged several times with syngas to remove air. The reactor content was then heated up to 110° C. under 200 kpag (2 barg) syngas pressure. Once the desired reaction temperature was reached, about 0.05 mol propylene was injected into the catalyst solution by means of synthesis gas and at the

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same time as the injection of propylene the pressure was adjusted to 1000 kpag (10 barg). Immediately after the substrate injection and pressure adjustment, the progress of the reaction was followed by measuring the rate of gas consumption, indicated by the pressure decay (DELTA-P) in the high pressure syngas storage cylinder. The reaction was run for 3 hours and at the end of the reaction the gas supply was stopped and the reactor was cooled down to room temperature. A gas sample was taken from the gas phase inside the reactor and analysed on a HP6890 gas chromatograph (supplied by Hewlett-Packard). The chromatograph was equipped with a thermal conductivity detector (TCD) detection system and a poraplotQ column of 30 m length, 0.53 mm internal diameter (ID), 10 μm df (standing for "dense phase" and indicating film thickness). A liquid sample was withdrawn from the reactor into a cooled sample vial and analysed for product composition by gas chromatography using a HP6890 gaschromatograph equipped with a Flame Ionisation Detector (FID) detection system and a wall coated open tubular (WCOT) Ultimetal column of 10 m length, 0.53 mm ID, 0.17 μm df. The column (HTSimdistCB) is a chemically bound high temperature simulated distillation column. "Ultimetal" and "poraplotQ" are trade names of the Varian-Chrompack company. For the determination of dimethyl ether a second analysis was carried out over a Chrompack CP Wax 52 fused silica column of 50 m length, 0.25 mm ID, 0.2 μm df. Sulfur analyses of the products were performed on a HP6890 gas chromatograph equipped with a fused silica column and a model 355 flameless sulphur chemoluminescence detector from Sievers. The column was a CPSIL5CB chemically bound silica column supplied by Chrompack of 30 m length, 0.32 mm ID and 5 μm df. This method gives quantitative information both about total sulfur and about individual sulphur components in the product with a detection limit of about 5 wtppb. Finally the reactor was depressurised and the liquid recovered and weighed. From the weight of the product, its composition and the composition of the offgas the end-conversion was calculated. The conversion at any given moment could then be calculated pro-rata the pressure drop at that moment, the measured end-conversion and the total pressure drop achieved at the end of the experiment. Two experiments served as reference case, providing a base case reaction rate for propylene hydroformylation with rhodium and triphenyl phosphine in absence of any impurity. The two runs also served to demonstrate the reproducibility of the experiments and the results of these experiments are shown in Tables 2 and 3. In those Tables, TPP stands for triphenyl phosphine; TPPO stands for triphenyl phosphine oxide; and TEGDE stands for tetra-ethylene glycol dimethyl ether (also known as tetraglyme). At 110° C. the graphs of ln(1-conversion) versus time in FIGS. 3 and 4 showed a linear slope, and first order reaction rates of 2.22 h-1 and 2.35 h-1 were measured respectively for the two reference runs. TABLE 2 Propylene reference run 1 PRODUCT COMPOSITION Wt percent g moles Propylene 0.01 0.02 0.0005 i-butanal 0.48 1.00 0.0139 n-butanal 1.85 3.86 0.0536 TPP 9.43 19.70 0.0751 TPPO 0.48 1.00 0.0036 Butyric acid 0.03 0.06 0.0007 TEGDE 87.71 183.23 0.8243 C3 in off gas 0.0110 0.0003 Substrate conversion 98.80percent molar time, min DELTA P Conversion 1-conversion In(1-conv) 0 0.000 0.000 1.000 0.000 2 0.860 6.561 0.934 -0.068 3 1.290 9.842 0.902 -0.104 4 1.690 12.893 0.871 -0.138 5 2.090 15.945 0.841 -0.174 6 2.490 18.996 0.810 -0.211 7 2.860 21.819 0.782 -0.246 8 3.210 24.489 0.755 -0.281 10 3.930 29.982 0.700 -0.356 12 4.580 34.941 0.651 -0.430 14 5.180 39.519 0.605 -0.503 16 5.740 43.791 0.562 -0.576 18 6.270 47.834 0.522 -0.651 20 6.750 51.496 0.485 -0.724 23 7.420 56.608 0.434 -0.835 26 8.030 61.262 0.387 -0.948 30 8.730 66.602 0.334 -1.097 35 9.480 72.324 0.277 -1.285 40 10.110 77.130 0.229 -1.475 45 10.610 80.945 0.191 -1.658 50 11.060 84.378 0.156 -1.856 55 11.410 87.048 0.130 -2.044 60 11.690 89.184 0.108 -2.224 90 12.530 95.592 0.044 -3.122 120 12.830 97.881 0.021 -3.854 180 12.950 98.797 0.012 -4.420 TABLE 3 Propylene reference run 2 PRODUCT COMPOSITION Wt percent g moles Propylene 0.01 0.02 0.0005 i-butanal 0.43 0.90 0.0125 n-butanal 1.67 3.49 0.0484 TPP 9.27 19.39 0.0740 TPPO 0.55 1.15 0.0041 Butyric add 0.04 0.08 0.0009 TEGDE 88.03 184.16 0.8285 C3 in off gas 0.0083 0.0002 Substrate conversion 98.61percent molar time, min DELTA P Conversion 1-conversion In(1-conv) 0 0.000 0.000 1.000 0.000 2 0.890 7.732 0.923 -0.080 3 1.300 11.294 0.887 -0.120 4 1.680 14.596 0.854 -0.158 5 2.050 17.810 0.822 -0.196 6 2.400 20.851 0.791 -0.234 7 2.750 23.892 0.761 -0.273 8 3.090 26.846 0.732 -0.313 10 3.700 32.146 0.679 -0.388 12 4.280 37.185 0.628 -0.465 14 4.800 41.702 0.583 -0.540 16 5.300 46.046 0.540 -0.617 18 5.750 49.956 0.500 -0.692 20 6.170 53.605 0.464 -0.768 23 6.770 58.818 0.412 -0.887 26 7.290 63.335 0.367 -1.003 30 7.900 68.635 0.314 -1.159 35 8.550 74.282 0.257 -1.358 40 9.050 78.626 0.214 -1.543 45 9.640 83.752 0.162 -1.817 50 9.850 85.577 0.144 -1.936 55 10.070 87.488 0.125 -2.078 60 10.300 89.486 0.105 -2.252 90 11.100 96.437 0.036 -3.334 120 11.300 98.174 0.018 -4.003 180 11.350 98.609 0.014 -4.275 With hydrogen, [rhodium(I)(carbonyl)2(acetylacetonate)], bis [2-(2-methoxyethoxy)ethyl] ether, triphenylphosphine, Time= 3h, T= 110 °C , Product distribution / selectivity Patent; Caers, Raphael Frans; Beckers, Hubertus Joseph; Van Driessche, Eddy Theophyle Andrea; Martens, Luc Roger Marc; Godsmark, John Stephen; Shutt, John Richard; US2007/282133; (2007); (A1) English View in Reaxys 2 :In two further experiments, either 0.024 wt percent or 0.1 wt percent of dimethylether (DME) were injected in the catalyst solution, corresponding to molar ratios of DME/Rh of 20 and 82 respectively. First order reaction rates of 2.21 h-1 and 2.28 h-1 were measured, showing no significant change from the reference runs where no DME was present. It may be concluded that DME has no significant inhibiting effect on the hydroformylation rate of propylene in a low pressure rhodium system. In the final products of the second test, 0.12 wt percent of DME was measured by

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GC, proving that DME had not undergone any chemical reaction. The results which are shown in Tables 5 and 6 (and FIGS. 6 and 7) indicate that a high propylene content propylene feed obtained by the reaction of oxygenates to olefins and containing DME can be used with the associated benefits. TABLE 5 Effect of dimethylether at 20 to 1 on Rh PRODUCT COMPOSITION Wt percent g moles Propylene 0.004 0.04 0.0010 DME 0.03 0.06 0.0014 i-butanal 0.42 0.88 0.0122 n-butanal 1.25 2.68 0.0371 TPP 10.25 21.42 0.0817 TPPO 0.14 0.29 0.0011 Butyric acid 0.08 0.17 0.0019 TEGDE 87.81 183.52 0.8256 C3 in off gas 0.003 0.0001 Substrate conversion 99.46percent molar DME/Rh 19.8 molar time, min DELTA P Conversion 1-conversion In(1-conv) 0 0.000 0.000 1.000 0.000 2 0.600 6.501 0.935 -0.067 3 0.920 9.968 0.900 -0.105 4 1.240 13.435 0.866 -0.144 5 1.510 16.360 0.836 -0.179 6 1.810 19.610 0.804 -0.218 7 2.080 22.535 0.775 -0.255 8 2.330 25.244 0.748 -0.291 10 2.870 31.094 0.689 -0.372 12 3.270 35.428 0.646 -0.437 14 3.700 40.087 0.599 -0.512 16 4.080 44.204 0.558 -0.583 18 4.430 47.996 0.520 -0.654 20 4.800 52.005 0.480 -0.734 23 5.250 56.880 0.431 -0.841 26 5.670 61.431 0.386 -0.953 30 6.170 66.848 0.332 -1.104 35 6.690 72.482 0.275 -1.290 40 7.120 77.140 0.229 -1.476 45 7.450 80.716 0.193 -1.646 50 7.750 83.966 0.160 -1.830 55 7.960 86.241 0.138 -1.983 60 8.150 88.300 0.117 -2.146 90 8.780 95.125 0.049 -3.021 120 8.980 97.292 0.027 -3.609 180 9.180 99.459 0.005 -5.220 TABLE 6 Effect of dimethylether at 82 to 1 on Rh PRODUCT COMPOSITION Wt percent g moles Propylene 0.009 0.105 0.0025 DME 0.12 0.274 0.0060 i-butanal 0.30 0.632 0.0088 nbutanal 1.14 2.402 0.0333 TPP 10.14 21.281 0.0812 TPPO 0.21 0.485 0.0017 Butyric acid 0.03 0.000 0.0000 Tegde 88.03 185.500 0.8345 C3 in off gas 0.006 0.0001 Substrate conversion 98.80percent molar DME/Rh 81.6 molar time, min DELTA P Conversion 1-conversion In(1-conv) 0 0.000 0.000 1.000 0.000 2 0.570 7.122 0.929 -0.074 3 0.850 10.621 0.894 -0.112 4 0.830 10.371 0.896 -0.109 5 1.390 17.368 0.826 -0.191 6 1.640 20.492 0.795 -0.229 7 1.880 23.491 0.765 -0.268 8 2.120 26.490 0.735 -0.308 10 2.550 31.862 0.681 -0.384 12 2.990 37.360 0.626 -0.468 14 3.370 42.108 0.579 -0.547 16 3.740 46.732 0.533 -0.630 18 4.070 50.855 0.491 -0.710 20 4.370 54.603 0.454 -0.790 23 4.780 59.726 0.403 -0.909 26 5.130 64.100 0.359 -1.024 30 5.520 68.973 0.310 -1.170 35 5.900 73.721 0.263 -1.336 40 6.200 77.469 0.225 -1.490 45 6.510 81.343 0.187 -1.679 50 6.710 83.842 0.162 -1.823 55 6.900 86.216 0.138 -1.982 60 7.050 88.090 0.119 -2.128 90 7.550 94.338 0.057 -2.871 120 7.850 98.086 0.019 -3.956 180 7.900 98.711 0.013 -4.351 With hydrogen, [rhodium(I)(carbonyl)2(acetylacetonate)], bis [2-(2-methoxyethoxy)ethyl] ether, triphenylphosphine in dimethyl-ether, Time= 3h, T= 110 °C , Product distribution / selectivity Patent; Caers, Raphael Frans; Beckers, Hubertus Joseph; Van Driessche, Eddy Theophyle Andrea; Martens, Luc Roger Marc; Godsmark, John Stephen; Shutt, John Richard; US2007/282133; (2007); (A1) English View in Reaxys 2 :In a third experiment, about 250 wtppm methyl mercaptan was added to the catalyst solution to provide a S/Rh molar ratio of 20. The first order reaction rate of propylene hydroformylation dropped to 0.27 h-1 or a decrease of about 88-89percent. Methyl mercaptan is clearly a strong inhibitor in the hydroformylation of propylene with rhodium and triphenylphosphine at low pressure. In the final product 195 wtppm of the total sulphur was detected as original methyl mercaptan, while the rest of the sulfur had been transformed into heavier sulphur species. The results are shown in Table 4 and FIG. 5. TABLE 4 Effect of methylmercaptan PRODUCT COMPOSITION Wt percent g moles Propylene 0.35 0.73 0.0174 i-butanal 0.38 0.80 0.0110 n-butanal 1.52 3.18 0.0441 TPP 9.82 20.55 0.0784 TPPO 0.16 0.33 0.0012 Butyric acid 0.03 0.06 0.0007 TEGDE 87.72 183.60 0.8260 C3 in off gas 0.1700 0.0040 Substrate conversion 57.02percent molar Sulfur in product, wtppm 238 time, min DELTA P Conversion 1-conversion In(1-conv) 0 0.000 0.000 1.000 0.000 2 0.090 0.524 0.995 -0.005 3 0.120 0.699 0.993 -0.007 4 0.170 0.990 0.990 -0.010 5 0.220 1.281 0.987 -0.013 6 0.270 1.573 0.984 -0.016 7 0.370 2.155 0.978 -0.022 8 0.430 2.505 0.975 -0.025 10 0.550 3.203 0.968 -0.033 12 0.670 3.902 0.961 -0.040 14 0.780 4.543 0.955 -0.046 16 0.940 5.475 0.945 -0.056 18 1.060 6.174 0.938 -0.064 20 1.130 6.582 0.934 -0.068 25 1.580 9.203 0.908 -0.097 30 1.970 11.474 0.885 -0.122 35 2.320 13.513 0.865 -0.145 40 2.680 15.610 0.844 -0.170 50 3.450 20.094 0.799 -0.224 60 3.810 22.191 0.778 -0.251 90 5.240 30.520 0.695 -0.364 120 6.840 39.839 0.602 -0.508 180 9.790 57.021 0.430 -0.844 With methanethiol, hydrogen, [rhodium(I)(carbonyl)2(acetylacetonate)], bis [2-(2-methoxyethoxy)ethyl] ether, triphenylphosphine, Time= 3h, T= 110 °C , Product distribution / selectivity Patent; Caers, Raphael Frans; Beckers, Hubertus Joseph; Van Driessche, Eddy Theophyle Andrea; Martens, Luc Roger Marc; Godsmark, John Stephen; Shutt, John Richard; US2007/282133; (2007); (A1) English View in Reaxys OH HO

Rx-ID: 11000943 View in Reaxys 142/804

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Yield

Conditions & References

88 %

With sodium hypochlorite in acetonitrile, Time= 1.5h, T= 20 °C Khurana; Sharma; Gogia; Kandpal; Organic Preparations and Procedures International; vol. 39; nb. 2; (2007); p. 185 - 189 View in Reaxys OH HO

O O

Rx-ID: 11000944 View in Reaxys 143/804 Yield

Conditions & References

83 %, 2 %

With sodium hypochlorite in acetonitrile, Time= 0.25h, T= 20 °C Khurana; Sharma; Gogia; Kandpal; Organic Preparations and Procedures International; vol. 39; nb. 2; (2007); p. 185 - 189 View in Reaxys O HO O

Rx-ID: 11000959 View in Reaxys 144/804 Yield

Conditions & References

79 %

With sodium hypochlorite in acetonitrile, Time= 1.5h, T= 20 °C Khurana; Sharma; Gogia; Kandpal; Organic Preparations and Procedures International; vol. 39; nb. 2; (2007); p. 185 - 189 View in Reaxys

HO O

Rx-ID: 11103800 View in Reaxys 145/804 Yield

Conditions & References

32 %, 55 %, 10 %

With nitric acid in water, Time= 2h, T= 50 °C Svetlakov; Nikitin; Nikolaeva; Russian Journal of Organic Chemistry; vol. 43; nb. 5; (2007); p. 771 - 772 View in Reaxys

Rx-ID: 11163561 View in Reaxys 146/804 Yield

Conditions & References

46.7 % Chromat., 20.9 % Chromat., 2.3 % Chromat.

With dipotassium peroxodisulfate, [VO{(CH2CH2O)3}] in trifluoroacetic acid, Time= 20h, T= 80 °C , p= 38002.6Torr , Kinetics, Product distribution, Further Variations: Catalysts, Pressures, Temperatures, Reagents, reaction time, catalyst amount, radical traps Kirillova, Marina V.; Da Silva, Jose A. L.; Da Silva, Joao J. R. Frausto; Palavra, Antonio F.; Pombeiro, Armando J. L.; Advanced Synthesis and Catalysis; vol. 349; nb. 10; (2007); p. 1765 - 1774 View in Reaxys

O HO

O O

Rx-ID: 11220052 View in Reaxys 147/804

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Yield

Conditions & References With water in phosphate buffer, pH= 7.2, Enzyme kinetics Cummins, Ian; Landrum, Marie; Steel, Patrick G.; Edwards, Robert; Phytochemistry; vol. 68; nb. 6; (2007); p. 811 - 818 View in Reaxys

O HN

S O

Cl Cl

Rx-ID: 11243872 View in Reaxys 148/804 Yield

Conditions & References With water, T= 70 °C , Kinetics, Thermodynamic data Spillane, William J.; Malaubier, Jean-Baptiste; Tetrahedron Letters; vol. 48; nb. 43; (2007); p. 7574 - 7577 View in Reaxys O

N H

O Br

Rx-ID: 11243873 View in Reaxys 149/804 Yield

N H

O I

HO O

Rx-ID: 11243874 View in Reaxys 150/804 Yield

N H

O F

HO O

Rx-ID: 11243875 View in Reaxys 151/804 Yield

O O

O S

N H

HO O

Rx-ID: 11243876 View in Reaxys 152/804 Yield

Conditions & References With water, T= 70 °C , Kinetics, Thermodynamic data Spillane, William J.; Malaubier, Jean-Baptiste; Tetrahedron Letters; vol. 48; nb. 43; (2007); p. 7574 - 7577

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View in Reaxys

O HN O

S O

Rx-ID: 11243877 View in Reaxys 153/804 Yield

O F F

O F

N H

OH F

HO O

Rx-ID: 11243878 View in Reaxys 154/804 Yield

Yield

Conditions & References Non-Catalytic Homogeneous Oxidation of n-Hexane For a comparison, n-hexane oxidation was conducted using oxygen in the absence of a catalyst. The results are shown in FIGS. 1a and 1b. Reaction conditions were: 25 cm3 nhexane, 0.20 cm3 dichlorobenzene, 403 K, 0.4 MPa O2 and 0.3 MPa n-hexane. Both figures clearly suggest that the homogeneous oxidation of n-hexane experienced an induction period. The formation rate of hexyl peroxide (ROOH) started increasing significantly in 1 h and reached its maximum at about 4.5 h (FIG. 1b). The decrease of the net ROOH formation rate after 5 h indicated that its decomposition was larger than its formation. In comparison with ROOH, the induction period for ROH+RO (desired oxidation) products was relatively long (about 3 h vs. 1 h of ROOH, FIG. 1b), which is consistent with their formation from ROOH. The terminal selectivity among all ROOH was 8.2percent during this initial period. With oxygen in 1,2-dichloro-benzene, T= 129.84 °C , Product distribution / selectivity Patent; The Regents of the University of California; Exxon Mobil Research and Engineering Company; US2007/4944; (2007); (A1) English View in Reaxys Catalytic Oxidation of n-Hexane on Mn-Exchanged Zeolites Catalytic oxidation rates of n-hexane on Mn-exchanged ZSM-57 zeolite are given in FIGS. 2a and 2b. The presence of Mn-ZSM-57 decreases the prevalent ROOH concentrations and induction periods relative to those observed in homogeneous reactions. FIG. 3 gives the terminal regioselectivity of n-hexane oxidation on Mn-ZSM-5 and Mn-ZSM-57 catalysts as a function of n-hexane conversion (which increases with increased contact time) along with non-catalytic homogeneous oxidation under the same oxidation conditions for comparison. Terminal regioselectivities were 14percent (kprim/ksec=0.22) during the early stages (<0.5 h) on Mn-ZSM-57 and 24percent (kprim/ksec=0.42) on Mn-ZSM-5. These values are much higher than during non-catalytic (8.2percent; kprim/ksec=0.12) oxidation of n-hexane. Terminal regioselectivities decreased with increasing n-hexane conversion and approached values typical of reaction in non-catalytic media (9.2percent after 7 h on Mn-ZSM-5; 8.1percent after 7 h on Mn-ZSM-57). A decrease in terminal regioselectivity with increased n-hexane conversion was observed for other Mn-exchanged zeolites in similar experiments, namely Mn-mordenite and MnZSM-58. ZSM-58 has 8-ring open windows; mordenite has 12-ring open windows. They are suitable for use in oxidation catalysts of this invention in general, but are not as suitable for selective terminal oxidation of n-hexane. These intrinsic terminal selectivities are shown in FIG. 4 for zeolites with different channel/window size and for non-catalytic oxidation experiments, as a comparison. All samples tested except Mn-ZSM-58 showed some preferential terminal oxidation relative to the non-catalytic system, indicating that channel geometry can be used to influence the position of oxygen insertion. Terminal selectivities on 8-ring (ZSM-58: 0.44 nm; 8.4percent) and 12-ring (mordenite: 0.70 nm; 9.5percent) zeolites were not significantly different for n-hexane than for non-catalytic autoxidation (8.2percent).

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Much higher selectivities were obtained on 10-ring zeolites (ZSM-57: 0.54 nm; 14percent; and ZSM-5: 0.56 nm; 24percent). On the other hand, while Mn-zeolites give higher n-hexane oxidation rates than homogeneous systems, in comparative experiments H-zeolites, namely H-mordenite, H-ZSM-57 and H-ZSM-5, gave even lower rates than in the absence of a catalyst. The H-zeolites are thus believed to function as peroxide (ROOH) scavengers. Based on this information an experiment was carried out to ascertain whether some advantage might be obtained by this role of H-zeolites. Oxidation of n-hexane using an Mn-ZSM-5 catalyst was conducted as before. After one hour, the oxidation was stopped and cooled down to room temperature followed by addition of 0.1 g H-ZSM-5. The terminal selectivity vs. reaction time for the resumed reaction was monitored and is given in FIG. 5 along with the sole MnZSM-5 catalyzed reaction. FIG. 5 indicates a reproducible terminal selectivity of 24percent in 1 h for the two separate runs. The terminal selectivity decreased to 16percent during the cooling down, addition of H-ZSM-5, and restarting processes. In fact, the terminal regioselectivity of n-hexane oxidation was then maintained at 16percent for 3 h with the presence of H-ZSM-5. This is significantly greater than the sole Mn-ZSM-5 catalyzed oxidation, where the terminal selectivity declined to about 10percent at the same contact time (5 h, FIG. 5). With oxygen, H-ZSM-57 in 1,2-dichloro-benzene, T= 129.84 °C , Product distribution / selectivity Patent; The Regents of the University of California; Exxon Mobil Research and Engineering Company; US2007/4944; (2007); (A1) English View in Reaxys Catalytic Oxidation of n-Hexane on Mn-Exchanged Zeolites Catalytic oxidation rates of n-hexane on Mn-exchanged ZSM-57 zeolite are given in FIGS. 2a and 2b. The presence of Mn-ZSM-57 decreases the prevalent ROOH concentrations and induction periods relative to those observed in homogeneous reactions. FIG. 3 gives the terminal regioselectivity of n-hexane oxidation on Mn-ZSM-5 and Mn-ZSM-57 catalysts as a function of n-hexane conversion (which increases with increased contact time) along with non-catalytic homogeneous oxidation under the same oxidation conditions for comparison. Terminal regioselectivities were 14percent (kprim/ksec=0.22) during the early stages (<0.5 h) on Mn-ZSM-57 and 24percent (kprim/ksec=0.42) on Mn-ZSM-5. These values are much higher than during non-catalytic (8.2percent; kprim/ksec=0.12) oxidation of n-hexane. Terminal regioselectivities decreased with increasing n-hexane conversion and approached values typical of reaction in non-catalytic media (9.2percent after 7 h on Mn-ZSM-5; 8.1percent after 7 h on Mn-ZSM-57). A decrease in terminal regioselectivity with increased n-hexane conversion was observed for other Mn-exchanged zeolites in similar experiments, namely Mn-mordenite and MnZSM-58. ZSM-58 has 8-ring open windows; mordenite has 12-ring open windows. They are suitable for use in oxidation catalysts of this invention in general, but are not as suitable for selective terminal oxidation of n-hexane. These intrinsic terminal selectivities are shown in FIG. 4 for zeolites with different channel/window size and for non-catalytic oxidation experiments, as a comparison. All samples tested except Mn-ZSM-58 showed some preferential terminal oxidation relative to the non-catalytic system, indicating that channel geometry can be used to influence the position of oxygen insertion. Terminal selectivities on 8-ring (ZSM-58: 0.44 nm; 8.4percent) and 12-ring (mordenite: 0.70 nm; 9.5percent) zeolites were not significantly different for n-hexane than for non-catalytic autoxidation (8.2percent). Much higher selectivities were obtained on 10-ring zeolites (ZSM-57: 0.54 nm; 14percent; and ZSM-5: 0.56 nm; 24percent). On the other hand, while Mn-zeolites give higher n-hexane oxidation rates than homogeneous systems, in comparative experiments H-zeolites, namely H-mordenite, H-ZSM-57 and H-ZSM-5, gave even lower rates than in the absence of a catalyst. The H-zeolites are thus believed to function as peroxide (ROOH) scavengers. Based on this information an experiment was carried out to ascertain whether some advantage might be obtained by this role of H-zeolites. Oxidation of n-hexane using an Mn-ZSM-5 catalyst was conducted as before. After one hour, the oxidation was stopped and cooled down to room temperature followed by addition of 0.1 g H-ZSM-5. The terminal selectivity vs. reaction time for the resumed reaction was monitored and is given in FIG. 5 along with the sole MnZSM-5 catalyzed reaction. FIG. 5 indicates a reproducible terminal selectivity of 24percent in 1 h for the two separate runs. The terminal selectivity decreased to 16percent during the cooling down, addition of H-ZSM-5, and restarting processes. In fact, the terminal regioselectivity of n-hexane oxidation was then maintained at 16percent for 3 h with the presence of H-ZSM-5. This is significantly greater than the sole Mn-ZSM-5 catalyzed oxidation, where the terminal selectivity declined to about 10percent at the same contact time (5 h, FIG. 5). With oxygen, H-ZSM-5 in 1,2-dichloro-benzene, T= 129.84 °C , Product distribution / selectivity Patent; The Regents of the University of California; Exxon Mobil Research and Engineering Company; US2007/4944; (2007); (A1) English View in Reaxys Catalytic Oxidation of n-Hexane on Mn-Exchanged Zeolites Catalytic oxidation rates of n-hexane on Mn-exchanged ZSM-57 zeolite are given in FIGS. 2a and 2b. The presence of Mn-ZSM-57 decreases the prevalent ROOH concentrations and induction periods relative to those observed in homogeneous reactions. FIG. 3 gives the terminal regioselectivity of n-hexane oxidation on Mn-ZSM-5 and Mn-ZSM-57 catalysts as a function of n-hexane conversion

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(which increases with increased contact time) along with non-catalytic homogeneous oxidation under the same oxidation conditions for comparison. Terminal regioselectivities were 14percent (kprim/ksec=0.22) during the early stages (<0.5 h) on Mn-ZSM-57 and 24percent (kprim/ksec=0.42) on Mn-ZSM-5. These values are much higher than during non-catalytic (8.2percent; kprim/ksec=0.12) oxidation of n-hexane. Terminal regioselectivities decreased with increasing n-hexane conversion and approached values typical of reaction in non-catalytic media (9.2percent after 7 h on Mn-ZSM-5; 8.1percent after 7 h on Mn-ZSM-57). A decrease in terminal regioselectivity with increased n-hexane conversion was observed for other Mn-exchanged zeolites in similar experiments, namely Mn-mordenite and MnZSM-58. ZSM-58 has 8-ring open windows; mordenite has 12-ring open windows. They are suitable for use in oxidation catalysts of this invention in general, but are not as suitable for selective terminal oxidation of n-hexane. These intrinsic terminal selectivities are shown in FIG. 4 for zeolites with different channel/window size and for non-catalytic oxidation experiments, as a comparison. All samples tested except Mn-ZSM-58 showed some preferential terminal oxidation relative to the non-catalytic system, indicating that channel geometry can be used to influence the position of oxygen insertion. Terminal selectivities on 8-ring (ZSM-58: 0.44 nm; 8.4percent) and 12-ring (mordenite: 0.70 nm; 9.5percent) zeolites were not significantly different for n-hexane than for non-catalytic autoxidation (8.2percent). Much higher selectivities were obtained on 10-ring zeolites (ZSM-57: 0.54 nm; 14percent; and ZSM-5: 0.56 nm; 24percent). On the other hand, while Mn-zeolites give higher n-hexane oxidation rates than homogeneous systems, in comparative experiments H-zeolites, namely H-mordenite, H-ZSM-57 and H-ZSM-5, gave even lower rates than in the absence of a catalyst. The H-zeolites are thus believed to function as peroxide (ROOH) scavengers. Based on this information an experiment was carried out to ascertain whether some advantage might be obtained by this role of H-zeolites. Oxidation of n-hexane using an Mn-ZSM-5 catalyst was conducted as before. After one hour, the oxidation was stopped and cooled down to room temperature followed by addition of 0.1 g H-ZSM-5. The terminal selectivity vs. reaction time for the resumed reaction was monitored and is given in FIG. 5 along with the sole MnZSM-5 catalyzed reaction. FIG. 5 indicates a reproducible terminal selectivity of 24percent in 1 h for the two separate runs. The terminal selectivity decreased to 16percent during the cooling down, addition of H-ZSM-5, and restarting processes. In fact, the terminal regioselectivity of n-hexane oxidation was then maintained at 16percent for 3 h with the presence of H-ZSM-5. This is significantly greater than the sole Mn-ZSM-5 catalyzed oxidation, where the terminal selectivity declined to about 10percent at the same contact time (5 h, FIG. 5). With oxygen, Mn-ZSM-57 in 1,2-dichloro-benzene, T= 129.84 °C , Product distribution / selectivity Patent; The Regents of the University of California; Exxon Mobil Research and Engineering Company; US2007/4944; (2007); (A1) English View in Reaxys Catalytic Oxidation of n-Hexane on Mn-Exchanged Zeolites Catalytic oxidation rates of n-hexane on Mn-exchanged ZSM-57 zeolite are given in FIGS. 2a and 2b. The presence of Mn-ZSM-57 decreases the prevalent ROOH concentrations and induction periods relative to those observed in homogeneous reactions. FIG. 3 gives the terminal regioselectivity of n-hexane oxidation on Mn-ZSM-5 and Mn-ZSM-57 catalysts as a function of n-hexane conversion (which increases with increased contact time) along with non-catalytic homogeneous oxidation under the same oxidation conditions for comparison. Terminal regioselectivities were 14percent (kprim/ksec=0.22) during the early stages (<0.5 h) on Mn-ZSM-57 and 24percent (kprim/ksec=0.42) on Mn-ZSM-5. These values are much higher than during non-catalytic (8.2percent; kprim/ksec=0.12) oxidation of n-hexane. Terminal regioselectivities decreased with increasing n-hexane conversion and approached values typical of reaction in non-catalytic media (9.2percent after 7 h on Mn-ZSM-5; 8.1percent after 7 h on Mn-ZSM-57). A decrease in terminal regioselectivity with increased n-hexane conversion was observed for other Mn-exchanged zeolites in similar experiments, namely Mn-mordenite and MnZSM-58. ZSM-58 has 8-ring open windows; mordenite has 12-ring open windows. They are suitable for use in oxidation catalysts of this invention in general, but are not as suitable for selective terminal oxidation of n-hexane. These intrinsic terminal selectivities are shown in FIG. 4 for zeolites with different channel/window size and for non-catalytic oxidation experiments, as a comparison. All samples tested except Mn-ZSM-58 showed some preferential terminal oxidation relative to the non-catalytic system, indicating that channel geometry can be used to influence the position of oxygen insertion. Terminal selectivities on 8-ring (ZSM-58: 0.44 nm; 8.4percent) and 12-ring (mordenite: 0.70 nm; 9.5percent) zeolites were not significantly different for n-hexane than for non-catalytic autoxidation (8.2percent). Much higher selectivities were obtained on 10-ring zeolites (ZSM-57: 0.54 nm; 14percent; and ZSM-5: 0.56 nm; 24percent). On the other hand, while Mn-zeolites give higher n-hexane oxidation rates than homogeneous systems, in comparative experiments H-zeolites, namely H-mordenite, H-ZSM-57 and H-ZSM-5, gave even lower rates than in the absence of a catalyst. The H-zeolites are thus believed to function as peroxide (ROOH) scavengers. Based on this information an experiment was carried out to ascertain whether some advantage might be obtained by this role of H-zeolites. Oxidation of n-hexane using an Mn-ZSM-5 catalyst was conducted as before. After one hour, the oxidation was stopped and cooled down to room temperature followed by addition of 0.1 g H-ZSM-5. The terminal selectivity vs. reaction time for the resumed reaction was monitored and is given in FIG. 5 along with the sole MnZSM-5 catalyzed reaction. FIG. 5 indicates a reproducible terminal selectivity of 24percent in 1 h for the two separate

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runs. The terminal selectivity decreased to 16percent during the cooling down, addition of H-ZSM-5, and restarting processes. In fact, the terminal regioselectivity of n-hexane oxidation was then maintained at 16percent for 3 h with the presence of H-ZSM-5. This is significantly greater than the sole Mn-ZSM-5 catalyzed oxidation, where the terminal selectivity declined to about 10percent at the same contact time (5 h, FIG. 5). With oxygen, Mn-ZSM-58 in 1,2-dichloro-benzene, T= 129.84 °C , Product distribution / selectivity Patent; The Regents of the University of California; Exxon Mobil Research and Engineering Company; US2007/4944; (2007); (A1) English View in Reaxys Catalytic Oxidation of n-Hexane on Mn-Exchanged Zeolites Catalytic oxidation rates of n-hexane on Mn-exchanged ZSM-57 zeolite are given in FIGS. 2a and 2b. The presence of Mn-ZSM-57 decreases the prevalent ROOH concentrations and induction periods relative to those observed in homogeneous reactions. FIG. 3 gives the terminal regioselectivity of n-hexane oxidation on Mn-ZSM-5 and Mn-ZSM-57 catalysts as a function of n-hexane conversion (which increases with increased contact time) along with non-catalytic homogeneous oxidation under the same oxidation conditions for comparison. Terminal regioselectivities were 14percent (kprim/ksec=0.22) during the early stages (<0.5 h) on Mn-ZSM-57 and 24percent (kprim/ksec=0.42) on Mn-ZSM-5. These values are much higher than during non-catalytic (8.2percent; kprim/ksec=0.12) oxidation of n-hexane. Terminal regioselectivities decreased with increasing n-hexane conversion and approached values typical of reaction in non-catalytic media (9.2percent after 7 h on Mn-ZSM-5; 8.1percent after 7 h on Mn-ZSM-57). A decrease in terminal regioselectivity with increased n-hexane conversion was observed for other Mn-exchanged zeolites in similar experiments, namely Mn-mordenite and MnZSM-58. ZSM-58 has 8-ring open windows; mordenite has 12-ring open windows. They are suitable for use in oxidation catalysts of this invention in general, but are not as suitable for selective terminal oxidation of n-hexane. These intrinsic terminal selectivities are shown in FIG. 4 for zeolites with different channel/window size and for non-catalytic oxidation experiments, as a comparison. All samples tested except Mn-ZSM-58 showed some preferential terminal oxidation relative to the non-catalytic system, indicating that channel geometry can be used to influence the position of oxygen insertion. Terminal selectivities on 8-ring (ZSM-58: 0.44 nm; 8.4percent) and 12-ring (mordenite: 0.70 nm; 9.5percent) zeolites were not significantly different for n-hexane than for non-catalytic autoxidation (8.2percent). Much higher selectivities were obtained on 10-ring zeolites (ZSM-57: 0.54 nm; 14percent; and ZSM-5: 0.56 nm; 24percent). On the other hand, while Mn-zeolites give higher n-hexane oxidation rates than homogeneous systems, in comparative experiments H-zeolites, namely H-mordenite, H-ZSM-57 and H-ZSM-5, gave even lower rates than in the absence of a catalyst. The H-zeolites are thus believed to function as peroxide (ROOH) scavengers. Based on this information an experiment was carried out to ascertain whether some advantage might be obtained by this role of H-zeolites. Oxidation of n-hexane using an Mn-ZSM-5 catalyst was conducted as before. After one hour, the oxidation was stopped and cooled down to room temperature followed by addition of 0.1 g H-ZSM-5. The terminal selectivity vs. reaction time for the resumed reaction was monitored and is given in FIG. 5 along with the sole MnZSM-5 catalyzed reaction. FIG. 5 indicates a reproducible terminal selectivity of 24percent in 1 h for the two separate runs. The terminal selectivity decreased to 16percent during the cooling down, addition of H-ZSM-5, and restarting processes. In fact, the terminal regioselectivity of n-hexane oxidation was then maintained at 16percent for 3 h with the presence of H-ZSM-5. This is significantly greater than the sole Mn-ZSM-5 catalyzed oxidation, where the terminal selectivity declined to about 10percent at the same contact time (5 h, FIG. 5). With oxygen, Mn-ZSM-5 in 1,2-dichloro-benzene, T= 129.84 °C , Product distribution / selectivity Patent; The Regents of the University of California; Exxon Mobil Research and Engineering Company; US2007/4944; (2007); (A1) English View in Reaxys

N N

Rx-ID: 10078238 View in Reaxys 156/804 Yield 56 %

Conditions & References Stage 1: With toluene-4-sulfonic acid in acetonitrile, Time= 8h, Heating Stage 2: With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 10h, Heating Katritzky, Alan R.; Singh, Sandeep K.; Jiang, Rong; Tetrahedron; vol. 62; nb. 16; (2006); p. 3794 - 3797

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View in Reaxys

O O

Rx-ID: 10160281 View in Reaxys 157/804 Yield

Conditions & References

80 %, 3.8 %

With Ca(OCl)2, montmorillonite K-10 in chloroform, Time= 2.5h, T= 20 °C Movassagh, Barahman; Dahaghin, Ebrahim; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 45; nb. 6; (2006); p. 1541 - 1543 View in Reaxys

OH O

Rx-ID: 10197019 View in Reaxys 158/804 Yield

Conditions & References With sodium hydroxide, Pseudomonas sp. lipase, sodium chloride, T= 25 °C , pH= 8.0, Enzyme kinetics Chiou, Shyh-Ying; Cheng, Yu-Ru; Lu, Chun-Ping; Lin, Yan-Fu; Lin, Long-Yau; Lin, Gialih; JAOCS, Journal of the American Oil Chemists' Society; vol. 83; nb. 3; (2006); p. 201 - 207 View in Reaxys O O

Rx-ID: 10197527 View in Reaxys 159/804 Yield

HO O

NH 2

Rx-ID: 10280834 View in Reaxys 160/804 Yield

Conditions & References With potassium phosphate buffer, lyophilized Zea mays nitrilase ZmNIT2 EC 3.5.5.1 in water, Time= 14h, T= 30 °C , pH= 7.15, Title compound not separated from byproducts Mukherjee, Chandrani; Zhu, Dunming; Biehl, Edward R.; Parmar, Rajiv R.; Hua, Ling; Tetrahedron; vol. 62; nb. 26; (2006); p. 6150 - 6154 View in Reaxys

(v4)

O O

Ge HO

OH H

OH O

Rx-ID: 11116703 View in Reaxys 161/804 Yield

Conditions & References Stage 1: in benzene, T= 20 °C

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Stage 2: With sulfuric acid in diethyl ether, Further stages. Further byproducts. Title compound not separated from byproducts. Stepovik; Gulenova; Russian Journal of General Chemistry; vol. 76; nb. 2; (2006); p. 235 - 244 View in Reaxys

(v4)

O O

Si HO

Rx-ID: 11116706 View in Reaxys 162/804 Yield

Conditions & References

0.08 g, 0.12 g, 0.008 g, 0.048 g

Stage 1: in benzene, T= 20 °C Stage 2: With (2,4-dinitro-phenyl)-hydrazine Stage 3: With sulfuric acid in diethyl ether, Further stages. Further byproducts. Stepovik; Gulenova; Russian Journal of General Chemistry; vol. 76; nb. 2; (2006); p. 235 - 244 View in Reaxys

(v4)

O HO

OH O

Rx-ID: 11116707 View in Reaxys 163/804 Yield

Conditions & References Stage 1: in benzene, T= 20 °C Stage 2: With sulfuric acid in diethyl ether, Further stages. Title compound not separated from byproducts. Stepovik; Gulenova; Russian Journal of General Chemistry; vol. 76; nb. 2; (2006); p. 235 - 244 View in Reaxys

HO O

O O

O O O

O HO

O O

Rx-ID: 23739637 View in Reaxys 164/804

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Yield

Conditions & References 1; 2; 3; 4 :Example 1 To a 1 liter, four neck flask equipped with stirrer, immersion thermometer, sub-surface nitrogen sparge tube and a barrett trap with condenser was charged 330 grams n-hexanol, 180 grams citric acid and 50 ml heptane. The reaction mass was heated with a heating mantle to reflux (approx. 120° C.), and 1.5 grams of tetra-nbutyl titanate esterification catalyst was added. The reaction mass was esterified at 120-140° C. until the acidity was less than 2 mg KOH/g acidity. The pressure was lowered using a vacuum pump to 20 mm Hg thereby distilling off the excess n-hexanol and heptane azeotrope. The ester-containing reaction mass was then steam-stripped with live steam at a temperature of 130-140° C. and full vacuum until no residual n-hexanol was detectable by gas chromatography analysis. The ester-containing reaction mass is cooled to 90° C., and 0.4 grams concentrated sulfuric acid is added dropwise with stirring. N-butyric anhydride (166 grams) is added dropwise with stirring at a rate to maintain an acylation temperature of between 90-110° C. The acylation reaction mixture is stirred and allowed to proceed for 2 hours to make an acylated ester reaction mass. By-product butyric acid is removed with vacuum distillation at 110° C. The acylated ester reaction mass is cooled to 70° C. and neutralized to a pH of 10 with a sufficient quantity of a neutralizing solution containing 10percent aqueous sodium carbonate. The aqueous layer is decanted, and the acylated ester-containing organic product layer is washed once with 250 ml water. A bleaching and polishing solution containing 4 grams of 30percent hydrogen peroxide and 4 gram of magnesium silicate is added dropwise at 70° C. The bleaching/polishing steps are allowed to continue for 30 minutes at 70° C. The bleached and polished acylated ester mass is then dehydrated to less than 0.1percent water content by Karl Fischer titration using full vacuum. This acylated ester mass is filtered to remove magnesium silicate. The amount of 488 grams of colorless (20 APHA) and odorless product with an assay of 99.8percent is obtained.; Example 2 Tetra-n-butyl titanate esterification catalyst is replaced by 2.5 grams of tetra-n-butyl zirconate. The yield and product quality was essentially the same as example 1 (a colorless ester product of 40 APHA or less, no detectable odor by even a trained, human, perfume sampling expert, and a purity of at least 99.5 wt percent).; Example 3 Tetra-b-butyl titanate esterification catalyst was replaced by 2.5 grams zirconium carbonate (40percent ZrO2). The yield was 421 grams and the product quality was essentially the same as example 1.; Example 4 Tetra-n-butyl titanate was replaced by 1.5 grams of methanesulfonic acid. When the esterification with n-hexanol was less than 4 mg KOH/g acidity, the reaction mass was cooled and neutralized with 10percent aqueous sodium carbonate to a pH within the range of about 9-10. The aqueous phase was decanted, and the organic mass was vacuum steam stripped as in example 1 to remove excess n-hexanol until no nhexanol remained in the ester product as determined by gas chromatography analysis. The ester-containing reaction mass is cooled to 90° C., and 0.4 grams concentrated sulfuric acid is added dropwise with stirring. In drops, 166 grams of n-butyric anhydride is added with stirring at a rate sufficient to maintain a temperature between 90-110° C. The mass is stirred for 2 hours. Thereafter, by-product butyric acid is distilled off under full vacuum at 110° C. The reaction mass is cooled to 70° C. and neutralized to pH of 10 with 10percent aqueous sodium carbonate. The aqueous layer is decanted, and the organic ester layer is washed once with 250 ml water. The ester-containing product is then bleached and polished by adding 4 grams of 30percent hydrogen peroxide and 4 grams of magnesium silicate by dropwise addition at a temperature of 70° C. The bleaching/polishing step is allowed to continue for 30 minutes at 70° C. whereupon water is removed by Karl Fischer titration using full vacuum to a water concentration of less than 0.1percent by weight. The bleached and polished acylated ester reaction mass is filtered to remove magnesium silicate. An acylated citrate triester is obtained in the amount of 480 grams that is colorless (40 APHA) and odorless with an assay of 99.6percent. With sulfuric acid, Time= 2h, T= 90 - 110 °C , Product distribution / selectivity Patent; Day, James F.; US2006/94894; (2006); (A1) English View in Reaxys

O O

HO O

Rx-ID: 23832030 View in Reaxys 165/804 Yield

Conditions & References 2 :Five experiments were conducted using the above described procedure to evaluate gamma-Al2O3 in the synthesis of methyl methacrylate by oxidative dehydrogenation of propionic acid and dimethyl ether. A sample of 1/8" gammaAl2O3 extrudates, CS331-4, was obtained from United Catalysts, Inc. (UCI) and was described by the manufacturer

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as 99.6percent by weight Al2O3. It had a surface area of 175-275 m2/g and pore volume of 0.6 cm3/g. A portion of this catalyst support was crushed and sieved and 2.87 grams (5.0 cm3) loaded into a reactor tube as described above. In Examples 1 and 2 of Table 5, the temperature was 330°C and 350°C, respectively. At 350°C, this unmodified gamma-Al2O3 catalyst which typically has only Lewis acidity, showed 63percent conversion of PA and MMA, methacrylic acid (MAA), isobutyric acid (IBA) and MIB of 1.1percent, 0.8percent, 0.3percent and 0.8percent, respectively, as well as a MP (methyl propionate) selectivity of 92.0percent. This is a very high selectivity to useful products of 95.0percent. It has only a low methylation activity at the terminal carbon of 0.1 percent butyric acid selectivity. At the lower temperature of 330°C, the IBA and MAA selectivities increase to 0.7percent and 1.6percent, respectively, however, the MMA selectivity decreases to 0.6percent and the byproducts, acetaldehyde and diethylketone, both increase significantly. In Examples 1 and 2, it is shown that the desired products methyl propionate, methyl isobutyrate, methyl methacrylate, isobutyric acid and methacrylic acid are produced using gamma-Al2O3 catalyst with a combined selectivity at 350°C of 95.0percent at 63percent PA conversion and 64percent DME conversion. The DME/PA ratio was 0.82 and the DME/O2 ratio was 3.8. With oxygen, aluminum oxide, T= 350 °C , Product distribution / selectivity Patent; Air Products and Chemicals, Inc.; EP1659108; (2006); (A1) English View in Reaxys O O

O O

Rx-ID: 23832616 View in Reaxys 166/804 Yield

Conditions & References 3 :EXAMPLE 3 Hydrogenation process (experiments 11 to 16)Hydrogenation experiments were carried out as described in EXAMPLE 1. As reactant, 7 grams of lactone were injected into the heated reactor. In experiments 11, 12 and 14 to 16, ethanol in an amount such that the EPO <DP n="14"/>lactone to ethanol molar ratio is 1.0 was also injected into the reactor. Different lactones were used as reactants in different experiments. In experiments 11 to 14, gamma valerolactone was used as reactant; in experiment 15, delta hexanolactone was used as reactant; in experiment 16 (not according to the invention) , gamma butyrolactone was used as reactant. Gamma butyrolactone is a lactone that is not substituted at the ring-closing carbon atom. The catalysts were prepared as described in EXAMPLE 1. The resultant metal concentrations (wtpercent metal based on the total weight of the catalyst) and the metal salt used in the impregnation solutions are shown in Table 2. In experiment 14 (not according to the invention) , a commercially available catalyst comprising nickel on silica was used (KL6564 ex. Kataleuna) . The molepercent (based on moles lactone supplied to the reactor) of unconverted lactone and the sum of the moles of saturated ethyl ester and saturated acid formed are given in Table 2. In experiment 13 (no ethanol), only acid was formed. EPO <DP n="15"/>Table 1. Catalyst composition and composition of reaction product for the hydrogenation of ethyl With 10 wtpercent nickel/0.1 wtpercent platinum on silica and zeolite β, Product distribution / selectivity Patent; SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.; WO2006/67171; (2006); (A1) English View in Reaxys

O Cl

O F

HO O

F F

F OH F

F O

F HO

Rx-ID: 25920455 View in Reaxys 167/804 Yield

Conditions & References With NiF3, T= 5 °C , Electrochemical reaction, Further byproducts. Velayutham; Jayaraman; Kulangiappar; Ilayaraja; Babu, Y. Ram; Rao, P. Santhan; Reddy, S. Narayana; Babu, K. Victor; Noel; Journal of Fluorine Chemistry; vol. 127; nb. 8; (2006); p. 1111 - 1118 View in Reaxys OH

O HO

HO O

Rx-ID: 9307530 View in Reaxys 168/804

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Yield

Conditions & References

95 %, 4 %

With dihydrogen peroxide, Na12[WZn3(H2O)2(ZnW9O34)2], Time= 7h, T= 75 °C Sloboda-Rozner, Dorit; Witte, Peter; Alsters, Paul L.; Neumann, Ronny; Advanced Synthesis and Catalysis; vol. 346; nb. 2-3; (2004); p. 339 - 345 View in Reaxys With Na12[WZn3(H2O)2(ZnW9O34)2], dihydrogen peroxide, Time= 7h, T= 85 °C Sloboda-Rozner, Dorit; Alsters, Paul L.; Neumann, Ronny; Journal of the American Chemical Society; vol. 125; nb. 18; (2003); p. 5280 - 5281 View in Reaxys With SiW11Zn, dihydrogen peroxide in water, Time= 9h, T= 89.85 °C Wang, Jianmin; Yan, Liang; Li, Guixian; Wang, Xiaolai; Ding, Yong; Suo, Jishuan; Tetrahedron Letters; vol. 46; nb. 41; (2005); p. 7023 - 7027 View in Reaxys O N

O O

Rx-ID: 9783949 View in Reaxys 169/804 Yield

Conditions & References With NaOAc buffer, acetic acid, functional monolayer protected gold cluster in acetonitrile, T= 25 °C , Kinetics, Further Variations: pH-values, Catalysts Pengo, Paolo; Polizzi, Stefano; Pasquato, Lucia; Scrimin, Paolo; Journal of the American Chemical Society; vol. 127; nb. 6; (2005); p. 1616 - 1617 View in Reaxys O

HO O

Rx-ID: 9874451 View in Reaxys 170/804 Yield 53 % Spectr., 5 % Spectr., 9% Spectr.

Conditions & References With lithium perchlorate in N,N-dimethyl-formamide, Electrochemical reaction, Title compound not separated from byproducts Weiwer; Olivero; Dunach; Tetrahedron; vol. 61; nb. 7; (2005); p. 1709 - 1714 View in Reaxys

I O

HO O

Rx-ID: 10196730 View in Reaxys 171/804 Yield 100 % Turnov.

Conditions & References With tris-(trimethylsilyl)silane, 2-hydroxyethanethiol, 1,1'-azobis (cyclohexanecarbonitrile) in water, Time= 4h, T= 100 °C Postigo, Al; Ferreri, Carla; Navacchia, Maria Luisa; Chatgilialoglu, Chryssostomos; Synlett; nb. 18; (2005); p. 2854 - 2856; Art.No: Y06305ST View in Reaxys

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E Z

Rx-ID: 11027463 View in Reaxys 172/804 Yield

Conditions & References With Pseudomonas fluorescens IP01 meta-cleavage product hydrolase, Enzyme kinetics Fushinobu, Shinya; Jun, So-Young; Hidaka, Masafumi; Nojiri, Hideaki; Yamane, Hisakazu; Shoun, Hirofumi; Omori, Toshio; Wakagi, Takayoshi; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 3; (2005); p. 491 498 View in Reaxys

O O

HO O

Rx-ID: 23572173 View in Reaxys 173/804 Yield

Conditions & References 1 : Vapor Phase Hydrogenation of Maleic Anhydride The vapor phase hydrogenation of maleic anhydride was carried out in the same manner as in Example 1, using the catalyst obtained in Comparative Preparation Example 1, and the results are exhibited in Table 2. From Table 1 and Table 2 above, it can be seen that in catalyst CuO(76.5)SiO2(23.5) according to the prior arts, it took a long time for its catalytic activity to be stabilized, the change in conversion and selectivity according to the change of the reaction conditions was severe, and its selectivity was reduced under the operation conditions of high conversion rate above 99percent, as compared with the hydrogenation catalyst of the invention, CuO(a)ZnO(b)MnO2(c)SiO2(d). With hydrogen, Time= 24 - 1460h, T= 250.8 - 255.2 °C , p= 760.051 - 1520.1Torr , Conversion of starting material Patent; Lee, Jung-Ho; Kim, Hyung-Rok; Han, Yo-Han; Jeong, Suk-Jong; Choi, Nak-Mo; Woo, Hang-Soo; Kim, In-Ki; US2005/240033; (2005); (A1) English View in Reaxys 1 :Example 1; Vapor Phase Hydrogenation of Maleic Anhydride (MAn); After 144 ml of Catalyst 1 of Preparation Example 1 was charged into the lower portion of a stainless reactor having an inside diameter of 1 inch and a length of 1.2 m and 36 ml of Catalyst 2 was charged into the upper portion of the reactor, they were slowly heated by flowing a 5percent H2/N2 mixed gas so that hot spots above 10° C. than reactor temperature did not occur, and then reduced at 300° C. for 12 hours. Thereafter, the temperature of the reactor was lowered, and 60 wt. percent of maleic anhydride containing gamma-butyrolactone solution was introduced as a mixed gas, which was prepared by spray-evaporating the maleic anhydride solution with hydrogen gas in an evaporator, while the mixed gas was supplied from the upper portion of the reactor. The performance results of the catalyst according to the change in reaction conditions are shown in Table 1. The abbreviations used in the above Table are as follows: WHSV: weight hourly space velocity; SAn: succinic anhydride; PrAL: propionaldehyde; PrOH: propanol; BuAL: butylaldehyde; THF: tetrahydrofuran; BuOH: butanol; PrA: propionic acid; BuA: Butanoic acid; GBL: gamma-butyrolactone. The conversion rate is represented on the basis of the amount of succinic anhydride (SAn), which is the first hydrogenation product, in order to indicate the degree of hydrogenation in a consecutive reaction, and the conversion rate of maleic anhydride itself showed to be almost 100percent. With hydrogen, Time= 24 - 432h, T= 251.1 - 255.2 °C , p= 760.051 - 2280.15Torr , Conversion of starting material Patent; Lee, Jung-Ho; Kim, Hyung-Rok; Han, Yo-Han; Jeong, Suk-Jong; Choi, Nak-Mo; Woo, Hang-Soo; Kim, In-Ki; US2005/240033; (2005); (A1) English View in Reaxys

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HO O

Rx-ID: 9645173 View in Reaxys 174/804 Yield

Conditions & References

80 %

With ruthenium(IV) oxide, Oxonereg;, sodium hydrogencarbonate in water, ethyl acetate, acetonitrile, Time= 1h, T= 20 °C Yang, Dan; Chen, Fei; Dong, Ze-Min; Zhang, Dan-Wei; Journal of Organic Chemistry; vol. 69; nb. 6; (2004); p. 2221 - 2223 View in Reaxys O

O O

Rx-ID: 9645174 View in Reaxys 175/804 Yield

Conditions & References With ruthenium(IV) oxide, Oxonereg;, sodium hydrogencarbonate in water, ethyl acetate, acetonitrile, Time= 0.333333h, T= 20 °C , Title compound not separated from byproducts Yang, Dan; Chen, Fei; Dong, Ze-Min; Zhang, Dan-Wei; Journal of Organic Chemistry; vol. 69; nb. 6; (2004); p. 2221 - 2223 View in Reaxys 3 Na +

–O

3 Na +

O– O

O O

O– O

–O

S O

O–

Rx-ID: 9708092 View in Reaxys 176/804 Yield

Conditions & References With peptide dendrimer [((Ac-Asp)2-B-His)2-B-Cys(Ser-NH2)]2 in various solvent(s), Time= 2h, T= 25 °C , pH= 6.0, Kinetics, Further Variations: Reagents Douat-Casassus, Celine; Darbre, Tamis; Reymond, Jean-Louis; Journal of the American Chemical Society; vol. 126; nb. 25; (2004); p. 7817 - 7826 View in Reaxys

HO O

Rx-ID: 25831253 View in Reaxys 177/804 Yield 52%

Conditions & References 41.B : Preparation of 1-ethyl-N-hydroxy 4-{[4-(3-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}propoxy)phenyl]sulfonyl}piperidine-4-carboxamide Hydrochloride Part B. In dry equipment under nitrogen, potassium trimethylsilanolate (10.52 g, 73.8 mmol) was dissolved in dimethylsulfoxide (40 mL) and gamma-butyrolactone (4.26 mL, 55.4 mmol) was added over 5 min while the reaction temperature rose to 49 C. After stirring at ambient temperature for 90 min, sodium hydride (2.2 g of a 60percent oil dispersion, 55.4 mmol) was added portion wise over 20 min and the reaction temperature rose to 38° C. Gas evolution was also observed. After stirring at ambient temperature for 40 min, a solution of the N-ethyl piperidine from Part A (12.66 g, 36.9 mmol) in dimethylsulfoxide (10 mL) was added over 10 min as the reaction rose to 8° C. The reaction was stirred at ambient temperature for t30 min.

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The slurry was slowly poured into ice water (400 mL) and then extracted with hexanes (100 mL) two times followed by a diethyl ether extraction (100 mL). The aqueous layer was chilled to 5° C. and the pH adjusted to 7 with concentrated hydrochloric acid. The aqueous solution was extracted with methylene chloride (150 mL) until there was no UV activity in the extract. The combined methylene chloride extracts were washed with saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated in vacuo. The solid was recrystallized from isopropanol (65 mL) to give the butyric acid as a white solid (8.2 g, 52percent). LCMSm/z=428 [M+H]+. in diethyl ether, dimethyl sulfoxide Patent; Freskos, John N.; Fobian, Y vette M.; Awasthi, Alok K.; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Carroll, Jeffery N.; Chandrakumar, Nizal S.; DeCrescenzo, Gary A.; Desai, Bipin N.; Heron, Marcia I.; Hockerman, Susan L.; Jull, Sara M.; Kassab, Darren J.; Kolodziej, Steve A.; McDonald, Joseph; Mischke, Deborah A.; Mullins, Patrick B.; Norton, Monica B.; Rico, Joseph G.; Talley, John J.; Trivedi, Mahima; Villamil, Clara I.; Wang, Lijuan Jane; US2004/24024; (2004); (A1) English View in Reaxys Cl Cl O

O O

S N

O OH

Rx-ID: 25896552 View in Reaxys 178/804 Yield 94%

Conditions & References 8 : Butanoic Acid, 1-[(1R)-1-[1-[(5-chloro-2-fluorophenyl)[(4-chlorophenyl)sulfonyl]amino]ethyl]butyl Ester (Isomer A) EXAMPLE 8 Butanoic Acid, 1-[(1R)-1-[1-[(5-chloro-2-fluorophenyl)[(4-chlorophenyl)sulfonyl]amino]ethyl]butyl Ester (Isomer A) To dichloromethane (20 mL) at room temperature was added 4-chloro-N-(2-fluoro-5-chlorophenyl)-N-(1R)-(2-hydroxy-1-methylpentyl)benzenesulfonamide (isomer A, 100 mg, 0.24 mmol), triethylamine (0.1 mL, 0.5 mmol), 4-(dimethylamino)pyridine (10 mg, 0.08 mmol), and butyric anhydride (48 mg, 0.3 mmol). After 48 h the reaction was diluted with dichloromethane and washed with 1N HCl, H2O, and brine. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (10percent EtOAc/hexanes) of the concentrate afforded the title compound as a white wax (110 mg, 94percent yield): 1H NMR (CDCl3) δ 7.69 (d, 2H, J=8.0 Hz), 7.44 (d, 2H, J=8.0 Hz), 7.31-7.35 (m, 1H), 6.99-7.18 (m, 2H), 4.79-4.81 (m, 1H), 4.46-4.53 (m, 1H), 3.11-3.27 (m, 2H), 1.26-1.66 (m, 6H), 1.13 (d, 3H, J=6.6 Hz), 0.83-0.95 (m, 6H). With dmap, triethylamine in dichloromethane Patent; Smith, David W.; Parker, Michael F.; US2004/97572; (2004); (A1) English View in Reaxys O

δ-Amino carboxylic acid

NaHCO3/THF

HO O

Rx-ID: 25896669 View in Reaxys 179/804 Yield 798 mg (90%)

Conditions & References N-maleinimido Butanoic Acid N-maleinimido Butanoic Acid δ-Amino carboxylic acid (500 mg, 4.84 mmol) is dissolved in 20 ml saturated NaHCO3 solution/THF (1:1). N-(methoxycarbonyl)maleinimide (910 mg, 5.81 mmol) is added portion-wise at 0° C.

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Following 10 min. at 0° C. the temperature is raised to room temperature and 20 ml saturated NaHCO3/THF solution (1:1) are added every hour. After 3 h, extraction using acetic acid ethyl ester (3*100 ml) is carried out and the organic phase is washed with saturated NaCl solution (1*100 ml). The organic phase is dried with magnesium sulfate and the solvent is removed in vacuo. Chromatography on silica gel (EtOAc) supplies the desired compound as a colorless solid. Yield: 798 mg (90percent) in tetrahydrofuran Patent; Weissler, Manfred; Kliem, Hans-Christian; Sauerbrei, Bernd; Schmauser, Birgit; US2004/59101; (2004); (A1) English View in Reaxys

O F

O HO O

F F

Rx-ID: 9223844 View in Reaxys 180/804 Yield

Conditions & References With sodium hydrogencarbonate in acetone, Time= 12h, T= 20 °C Alonso, Diego A.; Najera, Carmen; Varea, Montserrat; Synthesis; nb. 2; (2003); p. 277 - 287 View in Reaxys

HO O

Rx-ID: 9519377 View in Reaxys 181/804 Yield

Conditions & References With ozone, Time= 5h, T= 100 °C , Product distribution, Further Variations: Temperatures, reaction times Syroezhko; Begak; Russian Journal of Applied Chemistry; vol. 76; nb. 6; (2003); p. 962 - 966 View in Reaxys H N

Rx-ID: 9785453 View in Reaxys 182/804 Yield

Conditions & References With copper(II) nitrate, sodium chloride, T= 25 °C , pH= 5, Kinetics, Further Variations: Reagents Huang, Ching-Hua; Stone, Alan T.; Environmental Science and Technology; vol. 37; nb. 9; (2003); p. 1829 - 1837 View in Reaxys

O O

HO OH

Rx-ID: 23052161 View in Reaxys 183/804 Yield

Conditions & References A : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the

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autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 platinum on carbon in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys 1 : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 Pt,3 Re,0.2 Sn on C in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys 2 : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 Pt,3 Re,0.4 Sn on C in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material

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Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys 3 : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 Pt,3 Re,0.6 Sn on C in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys 4 : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 Pt,3 Re,0.8 Sn on C in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys F : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent

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Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 Pt,0.8 Sn on C in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys C : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 Pt,3 Re on C in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys D : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 Pt,4 Re on C in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys E : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst

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percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 Pt,5 Re on C in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys B : Examples 1-4 The catalysts were prepared in-situ and tested simultaneously by adding to a 300-cc autoclave 0.4 g 1percent platinum/carbon precursor obtained from Aldrich (cat. No.20,592-3) and given amounts of Re2O5 and SnCl4 (as applicable) to give the catalyst compositions given in Table 1. Also, 125 g of 20percent aqueous GBL was added to the autoclave as the test solution. The autoclave was heated to 250° C. and then pressurized to 2000 psig (14.x.106 Pa gage) with H2, while stirring. The conditions were maintained for 45 min, after which it was rapidly cooled down and the products were analyzed by GC (gas chromatography) to determine the net molar production rate (STY), and molar selectivity. The results are shown in Table 1. [00033] The STY and Selectivity are defined as follows: [00034] STY=mol/Kg of catalyst-hr [00035] Molar Selectivity=(THF+BDO)STY/[(THF+BDO)STY+By-products STY] [00036] By-products=propanol+butanol+propionic acid+butyric acid[TABLE-US-00001] TABLE 1 Molar SelectivityEx.Catalyst percent on CTHF+BDO STYTHF+BDO A1percent Pt11.20.65B1percent Pt,1percent Re23.90.79C1percent Pt,3percent Re41.20.84D1percent Pt,4percent Re45.10.85E1percent Pt,5percent Re55.70.8711percent Pt,3percent Re, 0.2percent Sn33.00.9021percent Pt,3percent Re,04percent Sn40.70.9031percent Pt,3percent Re,0.6percent Sn26.90.9141percent Pt,3percent Re,0.8percent Sn40.00.91F1percent Pt,0.8percent Sn28.80.92 [00037] It can be observed from Table 1 that although adding rhenium to a platinum-carbon catalyst increases the catalytic activity and selectivity, the selectivity is further increased by the addition of tin. With hydrogen, 1 Pt,1 Re on C in water, Time= 0.75h, T= 250 °C , p= 103432Torr , Conversion of starting material Patent; E. I. du Pont de Nemours and Company; US6670490; (2003); (B1) English View in Reaxys

HO OH O

Rx-ID: 9174303 View in Reaxys 184/804 Yield

Conditions & References With dihydrogen peroxide, chromic acid in acetonitrile, Time= 1h, T= 60 °C , p= 750.06Torr , Product distribution Suess-Fink; Shul'Pin; Petroleum Chemistry; vol. 42; nb. 1; (2002); p. 15 - 19 View in Reaxys

HO O

Rx-ID: 9244060 View in Reaxys 185/804 Yield 85 %

Conditions & References With potassium permanganate, iron(III) chloride in acetone, Time= 29h, T= -78 - 20 °C Lai, Sheng; Lee, Donald G.; Tetrahedron; vol. 58; nb. 49; (2002); p. 9879 - 9887 View in Reaxys O HO

Rx-ID: 9244061 View in Reaxys 186/804

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Yield

Conditions & References

75 %, 21 %

With potassium permanganate, iron(III) chloride in acetone, Time= 15.5h, T= -78 - 20 °C Lai, Sheng; Lee, Donald G.; Tetrahedron; vol. 58; nb. 49; (2002); p. 9879 - 9887 View in Reaxys

O N

HN H 2N

OH OH

O O

H 2N

N O

Rx-ID: 9676532 View in Reaxys 187/804 Yield

Conditions & References With New Zealand albino male rabbit cornea homogenate in phosphate buffer, Time= 24h, T= 37 °C , Kinetics, Further Variations: Reagents Dias, Clapton S.; Anand, Banmeet S.; Mitra, Ashim K.; Journal of Pharmaceutical Sciences; vol. 91; nb. 3; (2002); p. 660 - 668 View in Reaxys O N

HN H 2N

O O

H 2N

N HN

N N

Rx-ID: 9676533 View in Reaxys 188/804 Yield

OH OH

OH O

O O H 2N

N HN

H 2N

N HN

N O

Rx-ID: 9681429 View in Reaxys 189/804 Yield

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View in Reaxys

N O

Rx-ID: 24057323 View in Reaxys 190/804 Yield

Conditions & References 48 : Butyric Acid, 3-Benzoyl-6-butyryloxy-2-nitro-phenyl Ester (Compound 20, Table 1) EXAMPLE 48 Butyric Acid, 3-Benzoyl-6-butyryloxy-2-nitro-phenyl Ester (Compound 20, Table 1) To a stirred solution of (3,4-dihydroxy-2-nitro-phenyl)-phenyl-methanone (0.34 g, 1.29 mmol) in dichloromethane (5 mL) at room temperature was added pyridine (0.41 g, 5.19 mmol), butyric anhydride (0.82 g, 5.19 mmol) and 4-dimethyl-aminopyridine (0.01 g). The resulting solution was stirred for one hour and then extracted by cold water, 1N HCl and brine, then dried over sodium sulphate. After filtration and evaporation in vacuo the residue was chromatographed over silica gel using an ethyl acetate/ petroleum ether mixture to give off-white crystals of m.p 55 to 57° C. With pyridine in dichloromethane, ethyl acetate, Petroleum ether Patent; Learmonth, David Alexander; Soares da Silva, Patricio Manuel Vierira Araujo; US2002/37931; (2002); (A1) English View in Reaxys

O HO

H O

Rx-ID: 8760275 View in Reaxys 191/804 Yield

O O

O H

HO O

Rx-ID: 8765773 View in Reaxys 192/804

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Yield

Conditions & References With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, lipase from Ophiostoma piliferum in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys

O HO

H O

Rx-ID: 8774514 View in Reaxys 193/804 Yield

O HO

Rx-ID: 8775671 View in Reaxys 194/804 Yield

O O

HO O

Rx-ID: 8775929 View in Reaxys 195/804 Yield

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With N,N-bis-2-(hydroxyethyl)-2-amino ethane sulfonic acid, lipase from Ophiostoma piliferum in water, T= 25 °C , pH= 7.20, Enzyme kinetics Liu, Andrew Man Fai; Somers, Neil A.; Kazlauskas, Romas J.; Brush, Terry S.; Zocher, Frank; Enzelberger, Markus M.; Bornscheuer, Uwe T.; Horsman, Geoff P.; Mezzetti, Alessandra; Schmidt-Dannert, Claudia; Schmid, Rolf D.; Tetrahedron Asymmetry; vol. 12; nb. 4; (2001); p. 545 - 556 View in Reaxys O HO

OH O

Rx-ID: 8809969 View in Reaxys 196/804 Yield

Conditions & References With (3RS,7R,11R)-phytanoyl-CoA, oxygen, iron(II) sulfate, Enzyme kinetics, Further Variations: Reagents Mukherji; Kershaw; MacKinnon; Clifton; Wierzbicki; Schofield; Lloyd; Chemical Communications; nb. 11; (2001); p. 972 - 973 View in Reaxys H N

H N

HO O

Rx-ID: 8809986 View in Reaxys 197/804 Yield

Conditions & References

68 % Chromat., 26 % Chromat.

With dihydrogen peroxide, bromine in 1,2-dichloro-ethane, Time= 3h, T= 20 °C

44 % Chromat., 46 % Chromat.

With hydrogen bromide, dihydrogen peroxide in 1,2-dichloro-ethane, Time= 3h, T= 20 °C

Bjorsvik; Fontana; Liguori; Minisci; Chemical Communications; nb. 6; (2001); p. 523 - 524 View in Reaxys

O HO

Rx-ID: 8871940 View in Reaxys 198/804 Yield

Conditions & References With dimethyl sulfoxide, palladium dichloride, Time= 32h, T= 60 °C , Further byproducts given Yusubov; Filimonov; Chi, Ki-Whan; Russian Chemical Bulletin; vol. 50; nb. 4; (2001); p. 649 - 653 View in Reaxys

Mg Cl

O HO

HO O

Rx-ID: 9065870 View in Reaxys 199/804 Yield

Conditions & References Stage 1: With [nickel(II)(pyridine)4(chloride)2] in tetrahydrofuran, T= 20 °C , Grignard reaction Stage 2: in tetrahydrofuran, Title compound not separated from byproducts Viktorov; Zubritskii; Russian Journal of General Chemistry; vol. 71; nb. 11; (2001); p. 1773 - 1785 View in Reaxys

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O HO

Rx-ID: 795836 View in Reaxys 200/804 Yield

Conditions & References

87 %

in water, Time= 0.25h, microwave irradiation, Decarboxylation Zara, Cynthia Lynn; Jin, Thomas; Giguere, Raymond J.; Synthetic Communications; vol. 30; nb. 12; (2000); p. 2099 - 2104 View in Reaxys in neat (no solvent), T= 141 °C , ΔH(excit.), ΔS(excit.), ΔF(excit.), Kinetics, Thermodynamic data Biswas, Mihir K.; Majumdar, Dilip K.; Journal of the Indian Chemical Society; vol. 58; (1981); p. 868 - 870 View in Reaxys Wislicenus; Urech; Justus Liebigs Annalen der Chemie; vol. 165; (1873); p. 95 View in Reaxys

H N

O O

Rx-ID: 5073218 View in Reaxys 201/804 Yield

Conditions & References With borate buffer in methanol, water, T= 37 °C , pH= 9.0, Hydrolysis, Kinetics, Further Variations: pH-values, Reagents, Temperatures Jordan, C. Geraldine M.; Journal of Pharmaceutical Sciences; vol. 86; nb. 10; (1997); p. 1085 - 1091 View in Reaxys in water, T= 37 °C , pH= 0.4, Kinetics, Further Variations: pH-values Nogowska; Acta Poloniae Pharmaceutica - Drug Research; vol. 57; nb. 5; (2000); p. 353 - 357 View in Reaxys

F C

F F

Rx-ID: 5219817 View in Reaxys 202/804 Yield

Conditions & References With dipotassium peroxodisulfate, magnesium, Time= 30h, T= 80 °C , p= 43320Torr , Carboxylation Asadullah, Mohammad; Kitamura, Tsugio; Fujiwara, Yuzo; Chemistry Letters; nb. 6; (1999); p. 449 - 450 View in Reaxys With dipotassium peroxodisulfate, bis(acetylacetonate)oxovanadium, anhydrous cobalt diacetate, Time= 15h, T= 80 °C , Carboxylation, Product distribution, Activation energy, Further Variations: Reagents, Temperatures, Pressures Asadullah, Mohammad; Taniguchi, Yuki; Kitamura, Tsugio; Fujiwara, Yuzo; Tetrahedron Letters; vol. 40; nb. 50; (1999); p. 8867 - 8871 View in Reaxys With dipotassium peroxodisulfate, calcium chloride, Time= 15h, T= 80 °C , p= 22501.8Torr , Carboxylation, Product distribution, Activation energy, Further Variations: Reagents, Pressures, Reaction partners Asadullah, Mohammad; Kitamura, Tsugio; Fujiwara, Yuzo; Journal of Catalysis; vol. 195; nb. 1; (2000); p. 180 186 View in Reaxys

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O N

O–

Rx-ID: 8555149 View in Reaxys 203/804 Yield

Conditions & References With calix[4]resorcinolarene tetraanion, water in N,N-dimethyl-formamide, T= 25 °C , Hydrolysis, Kinetics, Further Variations: Reagents Mirgorodskaya; Kudryavtseva; Kazakova; Konovalov; Russian Chemical Bulletin; vol. 49; nb. 2; (2000); p. 261 264 View in Reaxys Cl O–

Na + Cl

Rx-ID: 8562388 View in Reaxys 204/804 Yield

Conditions & References With water, glow dicharge plasma, Oxidation, dechlorination, Kinetics Sharma; Josephson; Camaioni; Goheen; Environmental Science and Technology; vol. 34; nb. 11; (2000); p. 2267 - 2272 View in Reaxys

OH O

O N O N

N O

Rx-ID: 8583427 View in Reaxys 205/804 Yield

Conditions & References With hydrogenchloride, citrate-phosphate-borate buffer in ethanol, T= 60 °C , pH= 9, Hydrolysis, Kinetics, Further Variations: pH-values Masson; Thorsteinsson; Sigurdsson; Loftsson; Pharmazie; vol. 55; nb. 5; (2000); p. 369 - 371 View in Reaxys

HO O

Rx-ID: 8676842 View in Reaxys 206/804 Yield

Conditions & References With oxygen, Time= 2h, T= 164.84 °C , p= 3750.38Torr , Product distribution, Kinetics Lindsay Smith, John R.; Nagatomi, Eiji; Waddington, David J.; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (2000); p. 2248 - 2258 View in Reaxys

Rx-ID: 8710276 View in Reaxys 207/804 Yield

Conditions & References With oxygen, Time= 1h, T= 164.84 °C , p= 3750.38Torr , Product distribution

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Lindsay Smith, John R.; Nagatomi, Eiji; Waddington, David J.; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (2000); p. 2248 - 2258 View in Reaxys

O O

Rx-ID: 8858889 View in Reaxys 208/804 Yield

Conditions & References With dihydrogen peroxide, chromic acid in acetonitrile, Time= 1h, T= 60 °C , p= 750.06Torr , Product distribution Shul'pin; Suess-Fink; Shul'pina; Journal of Chemical Research - Part S; nb. 12; (2000); p. 576 - 577 View in Reaxys N N

H 2N

S O

O O

Rx-ID: 24431835 View in Reaxys 209/804 Yield 90%

Conditions & References 15 : Butanoic acid, 2-(5-methyl-6-methylthio-3-pyridinecarboxamido)-3-oxo, ethyl ester STR23 Example 15 Butanoic acid, 2-(5-methyl-6-methylthio-3-pyridinecarboxamido)-3-oxo, ethyl ester STR23 To a stirred suspension of 5-methyl-6-methylthio-3-pyridinecarboxamide (0.83 g, 4.6 mmol) in dry chloroform (120 mL) at room temperature under a nitrogen atmosphere was added rhodium (II) acetate (0.04 g, 0.09 mmol), and the reaction mixture was heated to reflux. A solution of ethyl diazoacetoacetate (1.00 g, 6.4 mmol) in dry chloroform (65 mL) was added dropwise over 6 h to the refluxing reaction mixture. After addition, the reaction mixture was kept at reflux for 30 min. The heat was removed and the reaction mixture was allowed to cool to room temperature overnight with stirring. Chromatographed on silica gel (25percent EtOAc/pentane) provided the desired product (0.87 g, 90percent) as a light yellow solid. With rhodium (II) acetate in chloroform Patent; Kirby; Neil V.; Morrison; Irene M.; Canada; Emily J.; Pieczko; Mary E.; Gustafson; Gary D.; Cooper; David H.; Adamski; Jenifer L.; Mathieson; John T.; Galka; Christopher S.; US6133294; (2000); (A1) English View in Reaxys

HO OH

Rx-ID: 2789000 View in Reaxys 210/804 Yield

Conditions & References With bromamine T in perchloric acid, Time= 10h, T= 24.9 °C , various temperature, Kinetics, Mechanism, Thermodynamic data Banerji, Kalyan K.; Tetrahedron; vol. 43; nb. 24; (1987); p. 5949 - 5954 View in Reaxys With potassium permanganate, perchloric acid, sodium fluoride in water, T= 29.9 °C , ΔG(excit.), ΔH(excit.), ΔS(excit.), other temperatures, Rate constant, Mechanism, Thermodynamic data Jain, Anandi L.; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 3; (1983); p. 678 - 692 View in Reaxys With N-bromobenzamide, mercury(II) diacetate in methanol, acetic acid, T= 24.9 °C , ΔH(excit.), ΔS(excit.), ΔG(excit.); other temp., Rate constant, Thermodynamic data Vyas, Vijay K.; Kothari, Seema; Banerji, Kalyan K.; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 35; nb. 2; (1996); p. 112 - 115

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View in Reaxys With benzyltrimethylammonium chlorobromate, acetic acid in dichloromethane, Time= 10h, T= 24.85 °C , Oxidation, Kinetics, Activation energy, Further Variations: Temperatures Bohra, Anupama; Sharma, P. K.; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 5; (1999); p. 1343 - 1356 View in Reaxys

HO O O NH O O–

O–

F F

N+ N+

Rx-ID: 5179173 View in Reaxys 211/804 Yield

Conditions & References With water, β-galactosidase, T= 37 °C , also in the presence of hog-liver esterase, other temp., Rate constant Geymayer, Paul; Bahr, Nicolaus; Reymond, Jean-Louis; Chemistry - A European Journal; vol. 5; nb. 3; (1999); p. 1006 - 1012 View in Reaxys

HO O

Rx-ID: 5204835 View in Reaxys 212/804 Yield 22 %, 14 %

Conditions & References With BF3·2HOAc in hexane, Time= 2.5h, Heating, Aldol-Grob reaction Kabalka; Li; Tejedor; Malladi; Gao; Trotman; Synthetic Communications; vol. 29; nb. 16; (1999); p. 2783 - 2787 View in Reaxys

L-2-amino-4-rsaquo;assym-NG

Rx-ID: 24228319 View in Reaxys 213/804 Yield 71%

Conditions & References 10 : L-2-Amino-4-assym-NG, NG[-dimethyl(guanidinooxy)] butanoic acid (9) Compound 9 (71percent yield) was obtained as a colorless solid utilizing the procedure described for the preparation of 8, but using dimethylcyanamide in place of 2-ethoxyimidazoline, m.p. 175.0°-177.0° (dec.); [α]D 23 =+4.6° (c=1.6, H2 O); 1 H-NMR (D2 O): δ3.98 (t, J=6.0 Hz, 2H, 4-CH2), 3.82 (t, J=6.0 Hz, 1H, 2-CH), 2.82 (s, 6H, 2*CH3) ppm; 13 CNMR (D2 O): δ177.90 (C-1), 162.80 (C=N), 72.26 (C-4), 55.39 (C-2), 39.49 (2*CH3), 32.73 (C-3) ppm; Anal. (C7 H16 N4 O3.0.25H 2 O) C,H,N. Patent; University of Kentucky Research Foundation; US5859295; (1999); (A1) English View in Reaxys

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O O

S NH

Rx-ID: 24239355 View in Reaxys 214/804 Yield

Conditions & References 9 : Preparation of N-Hydroxy-4-[(4-methylphenylsulfonylamino)-2-(4-methoxyphenylsulfonylamino)]butanamide. STR12 Step 1. The solution is adjusted to pH 6 and cooled at 5° C. to yield 0.5 g of the butyric acid, which is crystallized from ethyl acetate/methanol to give the title compound. (mp 128°-129° C.). Patent; Pharmacia and Upjohn Company; US5859061; (1999); (A1) English View in Reaxys

O–

N+ HO

S OO

F OH

OH F

HO O

Rx-ID: 36657502 View in Reaxys 215/804 Yield

Conditions & References With potassium permanganate in water, T= 65 - 70 °C Mahmood, Arshed; Robinson, Graham E.; Powell, Lyn; Organic Process Research and Development; vol. 3; nb. 5; (1999); p. 363 - 364 View in Reaxys

O C

HO O

Rx-ID: 1846487 View in Reaxys 216/804 Yield

Conditions & References With water, toluene-4-sulfonic acid, para-toluenesulphonic acid silver salt, palladium dichloride, sulfoxantphos, Time= 0.5h, T= 120 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Goedheijt, Marcel Schreuder; Reek, Joost N. H.; Kamer, Paul C. J.; Van Leeuwen, Piet W. N. M.; Chemical Communications; nb. 22; (1998); p. 2431 - 2432 View in Reaxys With water, bis-triphenylphosphine-palladium(II) chloride, iron(III) chloride in 1,4-dioxane, Time= 2h, T= 110 °C , p= 6000.5 - 15001.2Torr , other catalysts PdCl2(Ph3P)2/MCln/Ph3P, Product distribution Noskov, Yu. G.; Terekhova, M. I.; Petrov, E. S.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 6.2; (1990); p. 1336 - 1339,1195 - 1197 View in Reaxys With bis-triphenylphosphine-palladium(II) chloride, water, triphenylphosphine in 1,4-dioxane, T= 110 °C , p= 6000.5Torr , var. catalytic systems, var. pH, Rate constant, Product distribution Petrova, N. E.; Noskov, Yu. G.; Terekhova, M. I.; Petrov, E. S.; Russian Journal of General Chemistry; vol. 63; nb. 3.2; (1993); p. 478 - 480; Zhurnal Obshchei Khimii; vol. 63; nb. 3; (1993); p. 678 - 681 View in Reaxys

NH 2

Rx-ID: 3307711 View in Reaxys 217/804

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Yield 34 %

Conditions & References With ruthenium trichloride, potassium hydroxide, potassium peroxomonosulphate, Time= 24h, Ambient temperature Green, Graham; Griffith, William P.; Hollinshead, David M.; Ley, Steven V.; Schroeder, Martin; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1984); p. 681 686 View in Reaxys

With potassium hydroxide, dipotassium peroxodisulfate, ruthenium trichloride in water, Time= 24h Griffith, William P.; Reddy, Bharti; Shoair, Abdel G. F.; Suriaatmaja, Maria; White, Andrew J. P.; Williams, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 7; (1998); p. 2819 - 2826 View in Reaxys I O

O O

O E

Z I

Rx-ID: 4866096 View in Reaxys 218/804 Yield

Conditions & References With sodium nitrate, iodine in acetic acid, Time= 3h, T= 85 °C , Yield given. Yields of byproduct given Yusubov, Mehman S.; Perederina, Irina A.; Filimonov, Victor D.; Park, Tae-Ho; Chi, Ki-Whan; Synthetic Communications; vol. 28; nb. 5; (1998); p. 833 - 836 View in Reaxys

O HO

HO O

Rx-ID: 4930621 View in Reaxys 219/804 Yield

Conditions & References With 2-hydroxy-1,3-isoindolinedione, manganese(II) 2,4-pentanedionate, oxygen in acetonitrile, Time= 6h, T= 50 °C , p= 760Torr , Yield given. Yields of byproduct given Sakaguchi, Satoshi; Takase, Tomoyuki; Iwahama, Takahiro; Ishii, Yasutaka; Chemical Communications; nb. 18; (1998); p. 2037 - 2038 View in Reaxys With copper acetylacetonate, 2-hydroxy-1,3-isoindolinedione, oxygen in acetonitrile, Time= 30h, T= 25 °C , p= 760Torr , other temperature and time, further transition metal complex, Product distribution Sakaguchi, Satoshi; Takase, Tomoyuki; Iwahama, Takahiro; Ishii, Yasutaka; Chemical Communications; nb. 18; (1998); p. 2037 - 2038 View in Reaxys With copper acetylacetonate, 2-hydroxy-1,3-isoindolinedione, oxygen in acetonitrile, Time= 30h, T= 25 °C , p= 760Torr , Yield given. Yields of byproduct given Sakaguchi, Satoshi; Takase, Tomoyuki; Iwahama, Takahiro; Ishii, Yasutaka; Chemical Communications; nb. 18; (1998); p. 2037 - 2038 View in Reaxys With 2-hydroxy-1,3-isoindolinedione, oxygen, cobalt(II) 2,4-pentanedionate in acetonitrile, Time= 6h, T= 50 °C , p= 760Torr , Yield given. Yields of byproduct given Sakaguchi, Satoshi; Takase, Tomoyuki; Iwahama, Takahiro; Ishii, Yasutaka; Chemical Communications; nb. 18; (1998); p. 2037 - 2038 View in Reaxys

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HO O

Rx-ID: 4931077 View in Reaxys 220/804 Yield

Conditions & References With PIPES buffer, Candida rugosa lipase in water, toluene, other enzymes, other solvent, Rate constant Um, Pil-Je; Drueckhammer, Dale G.; Journal of the American Chemical Society; vol. 120; nb. 23; (1998); p. 5605 5610 View in Reaxys

HO O

Rx-ID: 5007093 View in Reaxys 221/804 Yield

Conditions & References With boron trifluoride in hexane, Time= 2.5h, Heating, Yield given. Yields of byproduct given Kabalka, George W.; Tejedor, David; Li, Nan-Sheng; Malladi, Rama R.; Trotman, Sarah; Tetrahedron; vol. 54; nb. 51; (1998); p. 15525 - 15532 View in Reaxys

HO O

Rx-ID: 5092508 View in Reaxys 222/804 Yield

Conditions & References

77 % Chromat., 80 % Chromat.

With dihydrogen peroxide, methyltrioctylammonium tetrakis(oxodiperoxotungsto)phos in water, Time= 6h, T= 85 °C Antonelli, Ermanno; D'Aloisio, Rino; Gambaro, Mario; Fiorani, Tiziana; Venturello, Carlo; Journal of Organic Chemistry; vol. 63; nb. 21; (1998); p. 7190 - 7206 View in Reaxys

80 % Chromat., 77 % Chromat.

OH O

Rx-ID: 36555097 View in Reaxys 223/804 Yield 65 %, 10 %, 8 %

Conditions & References With dihydrogen peroxide, bromine in dichloromethane, water, Time= 4h, T= 20 °C Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 261 - 269 View in Reaxys

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O O

O HO OH

HO O

O HO

HO HO

H O H

HO OH

OH O

O OH

OH OH

O OH

OH HO

HO OH OH OH OH OH HO OH HO OH OH HO O H

OH O

H O H

O O

H OH

Rx-ID: 4741118 View in Reaxys 224/804 Yield

Conditions & References With phosphate buffer in water-d2, T= 25 °C , standard molar enthalpy ΔrH0, standard molar Gibbs energy ΔrG0, standard molar entropy ΔrS0, Equilibrium constant, Thermodynamic data Rekharsky, Mikhail V.; Mayhew, Martin P.; Goldberg, Robert N.; Ross, Philip D.; Yamashoji, Yuko; Inoue, Yoshihisa; Journal of Physical Chemistry B; vol. 101; nb. 1; (1997); p. 87 - 100 View in Reaxys

O O

Rx-ID: 4931637 View in Reaxys 225/804 Yield

Conditions & References T= 225 °C , various initial vapour pressures and surface-to-volume ratios; activation energy E, logA, ΔS(excit.); other temp., Rate constant Stepanov; Kruglyakova; Russian Journal of Organic Chemistry; vol. 33; nb. 10; (1997); p. 1395 - 1397 View in Reaxys O

Rx-ID: 5069525 View in Reaxys 226/804 Yield

Conditions & References

9.5 mg

With lithium hydroxide in tetrahydrofuran, Time= 6h, T= 22 °C , Hydrolysis Wipf, Peter; Wenjing, Xu; Hongyong, Kim; Takahashi, Hidenori; Tetrahedron; vol. 53; nb. 48; (1997); p. 16575 16596 View in Reaxys

O O

OH OH

HO O

Rx-ID: 5069901 View in Reaxys 227/804 Yield 23 mg

Conditions & References With lithium hydroxide in tetrahydrofuran, Time= 6h, T= 22 °C , Hydrolysis Wipf, Peter; Wenjing, Xu; Hongyong, Kim; Takahashi, Hidenori; Tetrahedron; vol. 53; nb. 48; (1997); p. 16575 16596 View in Reaxys

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H+

H N

O O

Rx-ID: 5077685 View in Reaxys 228/804 Yield

Conditions & References in methanol, water, T= 37 °C , pH= 7.4, Hydrolysis, Kinetics, Further Variations: pH-values Jordan, C. Geraldine M.; Journal of Pharmaceutical Sciences; vol. 86; nb. 10; (1997); p. 1085 - 1091 View in Reaxys

O O

Rx-ID: 8539757 View in Reaxys 229/804 Yield

Conditions & References

96 %

Stage 1: With pyridinium p-toluenesulfonate in methanol, water, Time= 1.5h, T= 22 °C , Ring cleavage Stage 2: With lithium hydroxide in tetrahydrofuran, Time= 6h, T= 22 °C , Hydrolysis Wipf, Peter; Wenjing, Xu; Hongyong, Kim; Takahashi, Hidenori; Tetrahedron; vol. 53; nb. 48; (1997); p. 16575 16596 View in Reaxys O

OH O

Rx-ID: 4562305 View in Reaxys 230/804 Yield 75 % Spectr., 15 % Spectr., 10 % Spectr.

Conditions & References With hydrogen, [RhCl(1,3,5-triaza-7-phosphaadamantane)3] in water-d2, T= 37 °C , pH 4.70, Product distribution Joo, Ferenc; Nadasdi, Levente; Benyei, Attila Cs.; Darensbourg, Donald J.; Journal of Organometallic Chemistry; vol. 512; nb. 1-2; (1996); p. 45 - 50 View in Reaxys

Rx-ID: 845499 View in Reaxys 231/804 Yield 74 %, 24 %

Conditions & References With Sodium bromate, lt;Ru2(napy)2(OH)Cl(H2O)4gt;lt;ClO4gt;4 in water, Time= 15h, T= 60 °C Boelrijk, Alexandra E. M.; Velzen, Maaike M. van; Neenan, Thomas X.; Reedijk, Jan; Kooijman, Huub; Spek, Anthony L.; Journal of the Chemical Society, Chemical Communications; nb. 23; (1995); p. 2465 - 2468 View in Reaxys

24 %, 74 %

With Sodium bromate, lt;Ru2(napy)2(OH)Cl(H2O)4gt;lt;ClO4gt;4 in water, Time= 15h, T= 60 °C Boelrijk, Alexandra E. M.; Velzen, Maaike M. van; Neenan, Thomas X.; Reedijk, Jan; Kooijman, Huub; Spek, Anthony L.; Journal of the Chemical Society, Chemical Communications; nb. 23; (1995); p. 2465 - 2468 View in Reaxys With air, mercury(II) diacetate, acetic acid, T= 30 - 50 °C , Reagens 4: Acetaldehyd Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944)

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View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys With air, acetic acid, bismuth triacetate, T= 30 - 50 °C , Reagens 4: Acetaldehyd Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys With vanadium (II) acetate, air, acetic acid, T= 30 - 50 °C , Reagens 4: Acetaldehyd Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys With air, Neutral lead acetate, acetic acid, T= 30 - 50 °C , Reagens 4: Acetaldehyd Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys

O O

Rx-ID: 1517915 View in Reaxys 232/804 Yield

Conditions & References With lt;RuCllt;(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthylgt;(benzene)gt;Cl ((S)-2), hydrogen, triethylamine in tetrahydrofuran, Time= 44h, T= 50 °C , p= 76000Torr , var. chiral catalysts, solvents and reaction times; also without Et3N; enantioselective catalytic hydrogenation, Product distribution Ohta, Tetsuo; Miyake, Tsutomu; Takaya, Hidemasa; Journal of the Chemical Society, Chemical Communications; nb. 23; (1992); p. 1725 - 1726 View in Reaxys With lt;RuCllt;(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthylgt;(benzene)gt;Cl ((S)-2), hydrogen, triethylamine in tetrahydrofuran, Time= 44h, T= 50 °C , p= 76000Torr , Title compound not separated from byproducts Ohta, Tetsuo; Miyake, Tsutomu; Takaya, Hidemasa; Journal of the Chemical Society, Chemical Communications; nb. 23; (1992); p. 1725 - 1726 View in Reaxys With hydrogen, lt;RuCl((S)-BINAP)(benzene)gt;Cl*0.9NEt3 in tetrahydrofuran, T= 50 °C , p= 76000Torr , Title compound not separated from byproducts Ohta, Tetsuo; Miyake, Tsutomu; Seido, Nobuo; Kumobayashi, Hidenori; Takaya, Hidemasa; Journal of Organic Chemistry; vol. 60; nb. 2; (1995); p. 357 - 363 View in Reaxys With lt;RuCllt;(R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthylgt;(benzene)gt;Cl, hydrogen, triethylamine in tetrahydrofuran, Time= 44h, T= 50 °C , p= 76000Torr , Title compound not separated from byproducts Ohta, Tetsuo; Miyake, Tsutomu; Takaya, Hidemasa; Journal of the Chemical Society, Chemical Communications; nb. 23; (1992); p. 1725 - 1726

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View in Reaxys With hydrogen, lt;RuCl((R)-BINAP)(benzene)gt;Cl*0.9NEt3 in tetrahydrofuran, T= 50 °C , p= 76000Torr , Title compound not separated from byproducts Ohta, Tetsuo; Miyake, Tsutomu; Seido, Nobuo; Kumobayashi, Hidenori; Takaya, Hidemasa; Journal of Organic Chemistry; vol. 60; nb. 2; (1995); p. 357 - 363 View in Reaxys

O O Cl

OH O

Rx-ID: 4066739 View in Reaxys 233/804 Yield

Conditions & References With ozone, Time= 0.166667h, T= 21 °C , var. of temp., conc., Ea, Rate constant, Thermodynamic data, Mechanism Rakovsky, S. K.; Cherneva, D. R.; Deneva, M.; International Journal of Chemical Kinetics; vol. 27; nb. 2; (1995); p. 153 - 166 View in Reaxys

Rx-ID: 4155540 View in Reaxys 234/804 Yield

Conditions & References With air, Titanium(IV) oxide, Time= 12h, p= 160Torr , Irradiation, role of O2 and photogenerated electron in oxidation reaction; effect of FeCl3 on the amount of CO2 produced, Mechanism Schwitzgebel, Joerg; Ekerdt, J. G.; Gerischer, H.; Heller, Adam; Journal of Physical Chemistry; vol. 99; (1995); p. 5633 - 5638 View in Reaxys

Rx-ID: 4248679 View in Reaxys 235/804 Yield

Conditions & References

50 % Turn- With 2-hydroxy-1,3-isoindolinedione, Co(acetylacetonate)3, oxygen in acetonitrile, Time= 5h, T= 65 °C ov., 16 % Iwahama, Takahiro; Sakaguchi, Satoshi; Nishiyama, Yutaka; Ishii, Yasutaka; Tetrahedron Letters; vol. 36; nb. Turnov. 38; (1995); p. 6923 - 6926 View in Reaxys 16 % Turn- With 2-hydroxy-1,3-isoindolinedione, Co(acetylacetonate)3, oxygen in acetonitrile, Time= 5h, T= 65 °C ov., 50 % Iwahama, Takahiro; Sakaguchi, Satoshi; Nishiyama, Yutaka; Ishii, Yasutaka; Tetrahedron Letters; vol. 36; nb. Turnov. 38; (1995); p. 6923 - 6926 View in Reaxys

(v2)

H Hg

HO O

Rx-ID: 4272041 View in Reaxys 236/804 Yield 37 %

Conditions & References Bellec, Nathalie; Guillemin, Jean-Claude; Tetrahedron Letters; vol. 36; nb. 38; (1995); p. 6883 - 6886 View in Reaxys

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HO O

Rx-ID: 4421575 View in Reaxys 237/804 Yield

Conditions & References With air, carbon, T= 300 °C , var. activated carbon as catalysts; also with UV radiation, Product distribution Barkauskas, Yu.; Kareiva, A.; Russian Journal of Applied Chemistry; vol. 68; nb. 3.2; (1995); p. 383 - 386; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 68; nb. 3; (1995); p. 441 - 445 View in Reaxys NH 2 O

O O

NH 2

Rx-ID: 24543361 View in Reaxys 238/804 Yield

Conditions & References

512 mg (98%)

32.B.A : Part A. ml) and dried (Na2 SO4) then concentrated to afford 512 mg (98percent) of desired product Butanoic Acid, 4-[[3[[[(1,1-dimethylethyl)amino]carbonyl](3-methylbutyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]amino]-2,2,3-trimethyl-4-oxo, [1S-[1R*(3S*),2S*]]-benzyl ester as a white solid, m/e=582(M+H). Patent; Monsanto Company; US5475013; (1995); (A1) English View in Reaxys

N+

Cl –

Rx-ID: 2428749 View in Reaxys 239/804 Yield

Conditions & References With water, Butyrylcholinesterase in 1,2-dichloro-ethane, T= 37 °C , effect of paraoxon on the inhibition of the enzyme butyrylcholinesteraseusing ion transfer across the interface between two immiscible liquids; further temperature (23 deg C), Rate constant Beattie; Infelta; Girault; Analytical Chemistry; vol. 66; nb. 1; (1994); p. 52 - 57 View in Reaxys

O O

O O O

O O

Rx-ID: 2896943 View in Reaxys 240/804 Yield 18 %, 20 %

Conditions & References With acetic anhydride, lt;bis(salicylidene-N-phenethyl)gt;cobalt(II) in acetonitrile, Time= 24h, T= 25 °C Punniyamurthy, T.; Bhatia, Beena; Iqbal, Javed; Journal of Organic Chemistry; vol. 59; nb. 4; (1994); p. 850 - 853 View in Reaxys

Z O

O racemate

racemate

HO O

Rx-ID: 3956442 View in Reaxys 241/804

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Yield

Conditions & References With sulfuric acid, dihydrogen peroxide, tris(cetyl)pyridinium 12-tungstophosphate in ethanol, chloroform, Time= 3h, Heating, Yield given. Further byproducts given. Yields of byproduct given Sakaguchi, Satoshi; Watase, Seiji; Katayama, Yuji; Sakata, Yasuyuki; Nishiyama, Yutaka; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 59; nb. 19; (1994); p. 5681 - 5686 View in Reaxys

O O

Rx-ID: 3956918 View in Reaxys 242/804 Yield

Conditions & References With water in acetonitrile, T= 20 °C , Rate constant Lyashchuk, S. N.; Skrypnik, Yu. G.; Russian Journal of Organic Chemistry; vol. 30; nb. 1.1; (1994); p. 10 - 17; Zhurnal Organicheskoi Khimii; vol. 30; nb. 1; (1994); p. 12 - 18 View in Reaxys

O O

O N

Rx-ID: 3961553 View in Reaxys 243/804 Yield

Conditions & References With Carbonate buffer, alpha-cyclodextrin in water, dimethyl sulfoxide, T= 25 °C , also with β-cyclodextrin, Rate constant Tee, Oswald S.; Mazza, Charles; Lozano-Hemmer, Rafael; Giorgi, Javier B.; Journal of Organic Chemistry; vol. 59; nb. 25; (1994); p. 7602 - 7608 View in Reaxys With phosphate buffer pH 11.6, dimethyl-β-cyclodextrin in water, T= 25 °C , without cyclodextrin reagent, Rate constant Tee, Oswald S.; Gadosy, Timothy A.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 10; (1994); p. 2191 - 2198 View in Reaxys

O O

OH O

Rx-ID: 4065365 View in Reaxys 244/804 Yield

Conditions & References

82.7 % Chromat., 6.1 % Chromat., 0.1 % Chromat., 0.5 % Chromat., 1.0 % Chromat.

With hydrogen, copper, magnesium, zinc, T= 244.9 °C , other catalyst; also succinic anhydride, dimethyl maleate and dimethyl succinate; var. temp., Mechanism, Product distribution Messori, Massimo; Vaccari, Angelo; Journal of Catalysis; vol. 150; nb. 1; (1994); p. 177 - 185 View in Reaxys

O O

Rx-ID: 4342109 View in Reaxys 245/804

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Yield

Conditions & References With sulfonic cation-exchange resin KU-23, T= -18.1 °C , var. temp., Equilibrium constant Kashkarova, I. B.; Rozhnov, A. M.; Verevkin, S. P.; Russian Journal of Applied Chemistry; vol. 67; nb. 9.1; (1994); p. 1305 - 1308; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 67; nb. 9; (1994); p. 1486 1490 View in Reaxys

O S

O–

N+

S OO

Rx-ID: 24499550 View in Reaxys 246/804 Yield

Conditions & References 15 : Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3.3.1.13,7 ]dec-2-yloxy)carbonyl]-amino]propyl]amino]ethyl]amino]-4-oxo-, chloromethyl ester, [R-(R*,R*)]- STR36 EXAMPLE 15 Butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3.3.1.13,7 ]dec-2-yloxy)carbonyl]-amino]propyl]amino]ethyl]amino]-4-oxo-, chloromethyl ester, [R-(R*,R*)]- STR36 To a suspension of [R-(R*,R*)]-4-[[2-[[3-(1H-indol-3-yl)-2-methyl-1-oxo-2-[[(tricyclo[3.3.1.13,7 ]dec-2-yloxy)carbonyl]amino]propyl]amino]-1-phenylethyl]amino]-4-oxobutanoic acid (CI-988) (500 mg, 0.81 mmol), sodium hydrogen carbonate (240 mg, 2.86 mmol), and tetrabutyl ammonium hydrogen sulphate (28 mg, 0.08 mmol) in CH2 Cl2 (5 ml) and water (5 mL) was added dropwise a solution of chloromethyl sulphonyl chloride (163 mg, 0.99 mmol) in CH2 Cl2 (3 mL). The mixture was stirred at room temperature for 5 hours and then 10percent citric acid solution and CH2 Cl2 were added. The organic phase was separated, dried (MgSO4), filtered, and evaporated. Purification by column chromatography on silica gel eluding with ethyl acetate/hexane mixtures gave butanoic acid, 4-[[2-[[3-(1H-indol-3-yl)-2-methyl-1 -oxo-2-[[(tricyclo[3,3,1,13,7 ]dec-2-yloxy)carbonyl]-amino]propyl]amino]ethyl]amino]-4-oxo-, chloromethyl ester, [R-(R*,R*)]- as an amorphous white solid (343 mg, 52percent), mp 155°.122° C. 300 MHz NMR (CDCl3 δ 1.42 (s, 3H), 1.50-1.60 (m, 2H), 1.70-2.00 (m, 12H), 2.55-2.80 (m, 4H), 3.25-3.40 (m, 3H), 3.47 (d, J 14.6 Hz, 1H), 4.00-4.15 (m, 1H), 4.89 (s, 1H), 5.20-5.30 (m, 2H), 5.60-5.70 (m, 2H), 6.30-6.40 (m, 1H), 6.95 (d, J 2.3 Hz, 1H), 7.05-7.40 (m, 10H), 7.56 (d, J 7.8 Hz, 1H), 8.46 (s, 1H). Analysis for C36 H43 ClNO6 0.5H2 O. Calcd: C, 64.32; H, 6.59; N, 8.33. Found: C, 64.14; H, 6.45; N, 8.23. With anhydrous sodium hydrogen carbonate, citric acid in dichloromethane, water Patent; Warner-Lambert Company; US5340825; (1994); (A1) English View in Reaxys

HO O

Rx-ID: 2000832 View in Reaxys 247/804 Yield

Conditions & References in tetrahydrofuran, T= 0 °C , Rate constant Yamazaki, Hiroyoshi; Hayashi, Nobuyoshi; Chemistry Letters; nb. 3; (1993); p. 525 - 528 View in Reaxys

Br H

(v3) N

O Br

HO O

Rx-ID: 4104785 View in Reaxys 248/804

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Yield

Conditions & References With acetic acid, T= -55.1 - 44.9 °C , ΔH(excit.), ΔS(excit.), and ΔG(excit.), Rate constant, Thermodynamic data Devi, Jai; Kothari, Seema; Banerji, Kalyan K.; Journal of Chemical Research, Miniprint; nb. 10; (1993); p. 2680 2694 View in Reaxys

I O

Rx-ID: 1782379 View in Reaxys 249/804 Yield

Conditions & References With sodium periodate, lt;Ni(OH)2lt;IO5(OH)gt;2gt;(6-), sulfuric acid, 1) aq. KOH, rt, 4 h, Yield given. Multistep reaction Dengel, Andrew C.; El-Hendawy, Ahmed M.; Griffith, William P.; Mostafa, Sahar I.; Williams, David J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 24; (1992); p. 3489 - 3496 View in Reaxys

HO O

Rx-ID: 1922639 View in Reaxys 250/804 Yield

Conditions & References With oxygen, Mn(II) stearate, T= 129.9 °C , other variable-valence metal stearates, Mechanism Opeida, L. I.; J. Appl. Chem. USSR (Engl. Transl.); vol. 65; nb. 12.2; (1992); p. 2826 - 2829,2353 - 2356 View in Reaxys

HO O

Rx-ID: 1938691 View in Reaxys 251/804 Yield

Conditions & References

25 %

With phosphate buffer, immobilized enzyme preparation from Rhodococcus sp, Time= 40h, Ambient temperature, pH 7.0 Raadt, Anna de; Klempier, Norbert; Faber, Kurt; Griengl, Herfried; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 1; (1992); p. 137 - 140 View in Reaxys OH O

O O

N O

Rx-ID: 2156418 View in Reaxys 252/804 Yield

Conditions & References With phosphate buffer, alpha-cyclodextrin, T= 25 °C , also in the presence of β-cyclodextrin, var. conc. of α-cyclodextrin, Rate constant Tee, Oswald S.; Du, Xian-Xian; Journal of the American Chemical Society; vol. 114; nb. 2; (1992); p. 620 - 627 View in Reaxys

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O N

O O

N OH

O O

Rx-ID: 2795321 View in Reaxys 253/804 Yield

Conditions & References With water in acetonitrile, T= 25 °C , Rate constant Kurono; Yamada; Hata; Okada; Takeuchi; Ikeda; Chemical and Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3715 - 3719 View in Reaxys With phosphate buffer, alpha-cyclodextrin, T= 25 °C , also in the presence of β-cyclodextrin, Rate constant Tee, Oswald S.; Du, Xian-Xian; Journal of the American Chemical Society; vol. 114; nb. 2; (1992); p. 620 - 627 View in Reaxys

HO O

Rx-ID: 1934619 View in Reaxys 254/804 Yield

Conditions & References With perchloric acid, bromamine T, ruthenium trichloride in water, T= 34.9 °C , Ea, log A, ΔH(excit.), ΔS(excit.), ΔG(excit.), disproportionation constant, Rate constant, Thermodynamic data Rao; Gowda; Journal of the Indian Chemical Society; vol. 68; nb. 4; (1991); p. 210 - 214 View in Reaxys

O HO

O O

Rx-ID: 2039721 View in Reaxys 255/804 Yield

Conditions & References With sodium hydroxide, water in ethanol, T= 30 °C , Rate constant Jackman; Petrei; Smith; Journal of the American Chemical Society; vol. 113; nb. 9; (1991); p. 3451 - 3458 View in Reaxys

OH O

Rx-ID: 3790451 View in Reaxys 256/804 Yield

Conditions & References

79 %

With triethyl borane, trifluorormethanesulfonic acid in 1,2,2-trifluoro-trichloroethane, a) -30 deg C, 30 min, b) room temperature, 6 h Olah; Wu; Synthesis; nb. 5; (1991); p. 407 - 408 View in Reaxys

(v3)

(v5)

O O Cu (v3) O OCu (v5)

(v3)

HO O

Rx-ID: 26847954 View in Reaxys 257/804

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Yield

Conditions & References in neat (no solvent), byproducts: CO2, H2, C; thermal decompn. at 300-350°C in vac.;; elem. anal.; Il'ina, E. G.; Santalova, N. A.; Dunaeva, K. M.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 36; (1991); p. 1297 - 1299; Zhurnal Neorganicheskoi Khimii; vol. 36; (1991); p. 2301 2305 ; (from Gmelin) View in Reaxys

(v3)

(v5)

O O Cu (v3) O OCu (v5)

(v3)

Cu +

(v3)

O–

Rx-ID: 26847955 View in Reaxys 258/804 Yield

Conditions & References in neat (no solvent), byproducts: CO, ketene; thermal decompn. on heating in vac. (4E-3 Torr) and at different N2pressures (5, 45, 135, 385 and 760 Torr) above 200°C; formation of a solid, trapping of volatile decompn. products in a receiver cooled with liquid N2;; elem. anal. of the solid product, IR of condensate; Il'ina, E. G.; Santalova, N. A.; Dunaeva, K. M.; Russian Journal of Inorganic Chemistry (Translation of Zhurnal Neorganicheskoi Khimii); vol. 36; (1991); p. 1297 - 1299; Zhurnal Neorganicheskoi Khimii; vol. 36; (1991); p. 2301 2305 ; (from Gmelin) View in Reaxys

O HO

HO OH

OH O

Rx-ID: 1733750 View in Reaxys 259/804 Yield

Conditions & References

24.9 mol, 38.0 mol, 20.0 mol, 33.9 mol

in water, T= 30 °C , Clostridium saccharoperbutylacetonicum DGN32, Further byproducts given. Title compound not

33.9 mol, 38.0 mol, 20.0 mol, 24.9 mol

in water, T= 30 °C , Clostridium saccharoperbutylacetonicum DGN32, Further byproducts given. Title compound not

separated from byproducts Hayashida, Shinsaku; Yoshino, Sadazo; Agricultural and Biological Chemistry; vol. 54; nb. 2; (1990); p. 427 - 435 View in Reaxys

HO O

HO OH

OH O

Rx-ID: 1733762 View in Reaxys 260/804 Yield

Conditions & References

0.8 mol, 6.9 mol, 20.4 mol, 79.9 mol

in water, T= 30 °C , Clostridium saccharoperbutylacetonicum N1-4, Further byproducts given. Title compound not

0.8 mol, 79.9 mol,

in water, T= 30 °C , Clostridium saccharoperbutylacetonicum N1-4, Further byproducts given. Title compound not

separated from byproducts Hayashida, Shinsaku; Yoshino, Sadazo; Agricultural and Biological Chemistry; vol. 54; nb. 2; (1990); p. 427 - 435 View in Reaxys

separated from byproducts

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20.4 mol, 6.9 mol

Hayashida, Shinsaku; Yoshino, Sadazo; Agricultural and Biological Chemistry; vol. 54; nb. 2; (1990); p. 427 - 435 View in Reaxys

O O

Rx-ID: 1910114 View in Reaxys 261/804 Yield

Conditions & References

32 %, 73 %, 26 %

With dihydrogen peroxide, tris(cetyl)pyridinium 12-tungstophosphate in tert-butyl alcohol, Time= 24h, Heating Ishii, Yasutaka; Sakata, Yasuyuki; Journal of Organic Chemistry; vol. 55; nb. 21; (1990); p. 5545 - 5547 View in Reaxys

32 %, 26 %, 73 %

O O

Rx-ID: 1910118 View in Reaxys 262/804 Yield

Conditions & References

15 %, 8 %, With dihydrogen peroxide, tris(cetyl)pyridinium 12-tungstophosphate in chloroform, Time= 24h, Heating 62 % Ishii, Yasutaka; Sakata, Yasuyuki; Journal of Organic Chemistry; vol. 55; nb. 21; (1990); p. 5545 - 5547 View in Reaxys 25 %, 5 %, With dihydrogen peroxide, tetrahexylammonium peroxotungstenphosphate in chloroform, Time= 24h, Heating 30 % Ishii, Yasutaka; Sakata, Yasuyuki; Journal of Organic Chemistry; vol. 55; nb. 21; (1990); p. 5545 - 5547 View in Reaxys With dihydrogen peroxide, peroxotungstenphosphate in chloroform, Time= 24h, Heating, different catalysts, different solvents, Product distribution Ishii, Yasutaka; Sakata, Yasuyuki; Journal of Organic Chemistry; vol. 55; nb. 21; (1990); p. 5545 - 5547 View in Reaxys

HO O

Rx-ID: 1933012 View in Reaxys 263/804 Yield

Conditions & References

75 %

With aluminium(III) iodide in acetonitrile, Time= 0.5h, Heating Mahajan; Dutta; Boruah; Sandhu; Tetrahedron Letters; vol. 31; nb. 27; (1990); p. 3943 - 3944 View in Reaxys

HO O

Rx-ID: 1940056 View in Reaxys 264/804 Yield

Conditions & References With sulfuric acid, water in 1,4-dioxane, T= 60 °C , Rate constant, Equilibrium constant Vojtko, J.; Zeitschrift fuer Physikalische Chemie (Leipzig); vol. 271; nb. 6; (1990); p. 1227 - 1235 View in Reaxys

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With emulsified substrate, water, acetic acid in various solvent(s), T= 30 °C , pH 4.20, Rate constant, Product distribution Diez, Tomas A.; Mata-Segreda, Julio F.; Phytochemistry (Elsevier); vol. 24; nb. 12; (1985); p. 3047 - 3048 View in Reaxys

HO O HO

OH HO

OH O

HO OH

CO2, H2, NADH

Rx-ID: 6727217 View in Reaxys 265/804 Yield

Conditions & References in water, T= 30 °C , Clostridium saccharoperbutylacetonium N1-4 and DGN32, Product distribution Hayashida, Shinsaku; Yoshino, Sadazo; Agricultural and Biological Chemistry; vol. 54; nb. 2; (1990); p. 427 - 435 View in Reaxys

Cl O

Rx-ID: 24879658 View in Reaxys 266/804 Yield

Conditions & References D.1 : Butanoic acid, 4-(4-chlorophenoxy)-3-oxo-, ethyl ester. EXAMPLE D1 Butanoic acid, 4-(4-chlorophenoxy)-3-oxo-, ethyl ester. To a mechanically stirred suspension of 64.3 g (1.5 mol) of NaH (56percent oil dispersion) in 600 mL of dry DMSO was added (with cooling) 77.14 g (59 mL, 0.6 mol) of 4-chlorophenol in 300 mL of dry DMSO followed by dropwise addition of 98.8 g (81 mL, 0.6 mol) of ethyl γ-chloroacetoacetate in 100 mL of dry DMSO. After 24 h at RT, the mixture was poured into 4 L of 0° C. H2 O, the resulting mixture was washed with hexane and then the pH was adjusted to 5-7 with 85percent H3 PO4 (a light yellow solid precipitated). The mixture was extracted with Et2 O (2x). The extracts were dried (MgSO4), and concentrated in vacuo and the resulting residue was recrystallized twice, first from ether:cyclohexane followed by ethyl acetate:hexane affording 69.18 g (45percent) of product as a yellow solid: mp 52°-55° C. With NaH in hexane, cyclohexane, dimethyl sulfoxide, ethyl acetate Patent; Monsanto Company; US4936905; (1990); (A1) English View in Reaxys

(Z,E)-2-brono-methyl-4-(2-methoxyphenoxy)methyl-1,3-dioxolane

HS O

HO O

Rx-ID: 24902062 View in Reaxys 267/804 Yield

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The combined extracts are dried on Na2 SO4, evaporated to dryness under vacuum to yield 3.2 g of 3-thia-4-/4-(2methoxy-phenoxy)-methyl-(Z,E)-(1,3)-dioxolan-2-yl/-butanoic acid (m.p. 62°-67° C.). Using in the same procedure, pure (Z) or (E)-2-bromomethyl-dioxolanes the following pure geometrical isomers 3thia-4-/4-(2-methoxyphenoxy)methyl-(Z)-(1,3)- dioxolan-2-yl/butanoic acid (m.p. 82°84° C.) and 3-thia-4-/4-/2-methoxyphenoxy)methyl-(E)-(1,3-dioxolan-2-yl/-butanoic acid (m.p. 78°-82° C.), are obtained. With sodium methylate in methanol Patent; Boehringer Mannhein Italia, S.p.A.; US4968706; (1990); (A1) English View in Reaxys O HO

E O

Rx-ID: 1910117 View in Reaxys 268/804 Yield

Conditions & References

1 %, 106 With dihydrogen peroxide, tris(cetylpyridinium) 12-molybdenophosph in water, 1,2-dichloro-ethane, Time= 13h, T= %, 22 %, 7 40 °C , other polyoxometalate catalysts, var. internal alkynes, Product distribution % Ballistreri, Francesco Paolo; Failla, Salvatore; Spina, Emanuela; Tomaselli, Gaetano Andrea; Journal of Organic Chemistry; vol. 54; nb. 4; (1989); p. 947 - 949 View in Reaxys H N

O N

HO O

Rx-ID: 2325499 View in Reaxys 269/804 Yield

Conditions & References With ozone in water, Time= 1.16667h, T= 40 °C , diff. concentrations of O3; diff. reaction time; influence of alkaline, Product distribution Berdin, Yu. S.; Zubarev, S. V.; Galutkina, K. A.; Devekki, A. B.; Proskuryakov, V. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 62; nb. 10.2; (1989); p. 2314 - 2317,2148 - 2151 View in Reaxys

O O

E O

O HO

E O

Rx-ID: 3726871 View in Reaxys 270/804 Yield

Conditions & References With potassium hydroxide in methanol, diethyl ether Bjornland, Terje; Liaaen-Jensen, Synnove,; Throndsen, Jahn; Phytochemistry (Elsevier); vol. 28; nb. 12; (1989); p. 3347 - 3354 View in Reaxys

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O O

methylmagnesium halogenide

Rx-ID: 6188393 View in Reaxys 271/804 Yield

Conditions & References

87 %

With copper(l) chloride in tetrahydrofuran, Time= 0.25h, T= 0 °C Kawashima, Masatoshi; Sato, Toshio; Fujisawa, Tamotsu; Tetrahedron; vol. 45; nb. 2; (1989); p. 403 - 412 View in Reaxys

HO Br

HBr

H O

Rx-ID: 8450218 View in Reaxys 272/804 Yield

Conditions & References in various solvent(s), T= -120.1 °C , Rate constant Clark, David R.; Emsley, John; Hibbert, Frank; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1989); p. 1455 - 1458 View in Reaxys

Rx-ID: 25196304 View in Reaxys 273/804 Yield

Conditions & References R.11 : (+-)-3-[2-(3-Indolyl)ethylcarbamoyl]-2-(1-naphthylmethyl)propionic acid To a solution of 1.45 g of the butyric acid obtained in 30 ml of dichloromethane was added 0.86 g of 1,1'-carbonyldiimidazole. in dichloromethane Patent; Kissei Pharmaceutical Co., Ltd.; US4863904; (1989); (A1) English View in Reaxys

O O

Rx-ID: 25461261 View in Reaxys 274/804 Yield

Conditions & References 15 : EXAMPLE 15 EXAMPLE 15 A solution of (E)-2-hydroxymethyl-4-(2-methoxyphenoxy) methyl-1,3-dioxolane in dimethylformamide (DMF) is added under nitrogen atmosphere to a suspension of sodium hydride (80percent in mineral oil, 0.57 g). The mixture is warmed at 40°C for 30-, and then cooled at 0-10°C, slowly added dropwise thereto a solution of ethyl bromoacetate (2.12 ml) in DMF. After 12 hours at room temperature, the reaction mixture is diluted with aqueous NaH2PO4 (100 ml) and extracted with ethyl acetate. After washing with water (3 x 30 ml) the organic phase is dried on Na2SO4 and evaporated under vacuum to give 2.7 g of ethyl 4-/(E)-4-(2-methoxy-phenoxy)methyl-(1,3)-dioxolane-2-yl/-3-oxa-butanoate as a clear oil(NMR CDCl3 1,2,3H (t) CH 3-CH2O; δ= 3.6,2H(d)- CH 2-O-CH2COOEt, δ =3,8,3H(s) CH 3 -O-, δ = 5,2,1H(t)-O-CH-O; δ = 6,8 4H(s) CH(aromatic). A suspension of this compound in aqueous NaOH N (20 ml) is stirred for 3 hours at room temperature to obtain a clear solution which is then extracted with ethyl acetate (2 x 10 ml) and the organic phase is discarded. The aqueous phase is acidified to pH 2,5-3 by treatment with a 10percent aqueous KHSO4 solution and extracted with ethyl acetate (5 x 10 ml).

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These organic extracts are collected, washed with water (2 x 10 ml) dried on Na2SO4 and concentrated to dryness under vacuum. The residue crystallizes from diisopropyl ether affording 2.0 g of 3-oxa-4-/4-(2-methoxy-phenoxy)methyl-(E) (1,3)-dioxolane-2-yl/butanoic acid; m.p.86-88°C. in N-methyl-acetamide, N,N-dimethyl-formamide, mineral oil Patent; BOEHRINGER MANNHEIM ITALIA S.P.A.; EP303227; (1989); (A1) English View in Reaxys (Z,E)-2-brono-methyl-4-(2-methoxy-phenoxy)methyl-1,3-dioxolane

Rx-ID: 25464313 View in Reaxys 275/804 Yield

Conditions & References 17 : EXAMPLE 17 EXAMPLE 17 A solution of methyl thioglycolate (1.62 ml) in methanol (5 ml) is added dropwise under an inert gas atmosphere to a stirred solution of sodium methoxide (from 0.46 g of Na) in methanol (40 ml); after 30 minutes 5 g of (Z,E)-2-bronomethyl-4-(2-methoxy-phenoxy)methyl-1,3-dioxolane are added dropwise to the mixture. The mixture is refluxed for 2 hours, diluted with aqueous 2N NaOH (8.5 ml) and heated again for 2 hours at the reflux temperature. After concentration to a small volume the mixture is diluted with water (20 ml) and washed with ethyl acetate and these extracts are discarded. The aqueous phase is then acidified to pH 2.5 (H2SO42N) and extracted with ethyl acetate (3 x 20 ml). The combined extracts are dried on Na2SO4, evaporated to dryness under vacuum to yield 3.2 g of 3-thia-4-/4-(2methoxy-phenoxy)-methyl-(Z,E)-(1,3)-dioxolan-2-yl/-butanoic acid (m.p. 62-67°C). Using in the same procedure, pure (Z) or (E)-2-bromomethyl-dioxolanes the following pure geometrical isomers: 3thia-4-/4-(2-methoxy-phenoxy)methyl-(Z)-(1,3)- dioxolan-2-yl/butanoic acid (m.p.82-84°C) and 3-thia-4-/4-2-methoxyphenoxy)methyl-(E)-(1,3) dioxolan-2-yl/-butanoic acid (m.p. 78-82°C), are obtained. With sodium methylate in methanol Patent; BOEHRINGER MANNHEIM ITALIA S.P.A.; EP303227; (1989); (A1) English View in Reaxys

OH O

Rx-ID: 1846531 View in Reaxys 276/804 Yield

Conditions & References With hydrogen, cobalt naphthene, T= 110 - 140 °C , isomerization of initial products, Product distribution Kuz'mina, L. S.; Maiorova, L. V.; Kharisov, M. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 61; nb. 3; (1988); p. 584 - 588,525 - 528 View in Reaxys

HO O

Rx-ID: 1940034 View in Reaxys 277/804 Yield

Conditions & References

25 (unit not With Horse Liver Esterase as Acetonic Powder in water, other enzyme (PPL), other ester, enzymatic discrimination given) of esters, Product distribution Jeso, B. De; Drouillard, S.; Degueil-Castaing, M.; Saux, A.; Maillard, B.; Synthetic Communications; vol. 18; nb. 14; (1988); p. 1691 - 1698

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View in Reaxys With emulsified substrate, water, acetic acid in various solvent(s), T= 30 °C , pH 4.20, Rate constant, Product distribution Diez, Tomas A.; Mata-Segreda, Julio F.; Phytochemistry (Elsevier); vol. 24; nb. 12; (1985); p. 3047 - 3048 View in Reaxys

HO O

Rx-ID: 1946058 View in Reaxys 278/804 Yield

Conditions & References With phosphate buffer, pig pancreatic lipase, pentan-3-yl butyrate in water, enzymatic discrimination of esters, Product distribution Jeso, B. De; Drouillard, S.; Degueil-Castaing, M.; Maillard, B.; Synthetic Communications; vol. 18; nb. 14; (1988); p. 1699 - 1706 View in Reaxys

Rx-ID: 2317955 View in Reaxys 279/804 Yield

Conditions & References

96 (unit not With Horse Liver Esterase as Acetonic Powder in water, other enzyme (PPL), enzymatic discrimination of esters, given), 4 Product distribution (unit not Jeso, B. De; Drouillard, S.; Degueil-Castaing, M.; Saux, A.; Maillard, B.; Synthetic Communications; vol. 18; nb. given) 14; (1988); p. 1691 - 1698 View in Reaxys

Rx-ID: 3248309 View in Reaxys 280/804 Yield

Conditions & References With phosphate buffer, pentyl butanoate, pig pancreatic lipase in water, enzymatic discrimination of esters, Product distribution Jeso, B. De; Drouillard, S.; Degueil-Castaing, M.; Maillard, B.; Synthetic Communications; vol. 18; nb. 14; (1988); p. 1699 - 1706 View in Reaxys O O

HO O

Rx-ID: 3260974 View in Reaxys 281/804 Yield

Conditions & References With Tris-HCl buffer, water, [45Ca]-Calcium cation, sodium chloride, Agkistrodon piscivorus piscivorus in acetonitrile, T= 37 °C , pH = 8.0, Rate constant Cho, Wonhwa; Markowitz, Michael A.; Kezdy, Ferenc J.; Journal of the American Chemical Society; vol. 110; nb. 15; (1988); p. 5166 - 5171 View in Reaxys

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H OH –

NH +4

NH 2

SH O

Rx-ID: 25031102 View in Reaxys 282/804 Yield

Conditions & References 34 : BUTANOIC ACID, 4-[[1-[[3-METHOXY-3-OXO-2(S)-[(TRIFLUOROACETYL)AMINO]PROPYL]THIO]-2-PENTADECYNYL]OXY]-, METHYL ESTER EXAMPLE 34 BUTANOIC ACID, 4-[[1-[[3-METHOXY-3-OXO-2(S)-[(TRIFLUOROACETYL)AMINO]PROPYL]THIO]-2-PENTADECYNYL]OXY]-, METHYL ESTER A stirred solution of the acetal-diester (1 g; from example 4) dissolved in dry CH2 Cl2 (6 ml) was treated with cysteine methylester N-triflouroacetamide (freshly prepared from 0.53 g corresponding disulfide). The mixture was cooled (cyclohexanone/dry ice bath) and the reaction flask was taken out of the cooling bath and let stir for 3-4 minutes followed by treatment with dilute (~7percent) NH4 OH. Extractive isolation with CH2 Cl2 gave a gummy product (1.4618 g) which was chromatographed on TLC grade silica gel (75 g) using 10percent acetone/n-Hexane as eluent. Fractions (5 ml each): 50-58 Pure less polar isomer (0.3783 g) 64-78 Pure more polar isomer (0.2626 g) Both isomers were obtained as thick oils. in dichloromethane, acetone Patent; Schering Corporation; US4758594; (1988); (A1) English View in Reaxys

CHCl3:MeOH

BF3 Et2 O

HO O

Rx-ID: 25053031 View in Reaxys 283/804 Yield

Conditions & References 37 : BUTANOIC ACID, 4,4'-[4E,6Z,9Z-PENTADECATRIEN-2-YNYLIDENE-BIS(THIO)]BISEXAMPLE 37 BUTANOIC ACID, 4,4'-[4E,6Z,9Z-PENTADECATRIEN-2-YNYLIDENE-BIS(THIO)]BISA solution of the product from preparative example IV (1.0 g) and 4-mercaptobutanoic acid (1.1 g) in 24 ml of dry CH2 Cl2 was cooled to -22° C. (CCl4 /CO2) (under N2). To this was added BF3 Et2 O (0.5 ml). The reaction mixture was stirred at this temperature for 2 hours. The mixture was diluted with CH2 Cl2 and washed with water. The organic phase was dried (Na2 SO4) and concentrated to provide the crude product which was purified by passing through 65 g of coarse SiO2 column, using CHCl3:MeOH:AcOH (990:9:1) as eluent to yield 0.98 g of product. With acetic acid in dichloromethane Patent; Schering Corporation; US4758594; (1988); (A1) English View in Reaxys

Me3 SiCl

SH O

HO O

Rx-ID: 25053032 View in Reaxys 284/804 Yield

Conditions & References 39 : BUTANOIC ACID, 4,4'-[2-PENTADECYNYLIDENEBIS(THIO)]BISEXAMPLE 39 BUTANOIC ACID, 4,4'-[2-PENTADECYNYLIDENEBIS(THIO)]BISThe product from preparative example II (1.58 g) and γ-mercaptobutyric acid (2.3 g) in 10 ml of dry CH2 Cl2 was treated with Me3 SiCl (1.0 ml) as in Example 38 to afford 1.35 g of product. in dichloromethane

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Patent; Schering Corporation; US4758594; (1988); (A1) English View in Reaxys

O–

2 O

Cl OO

(v4)Ru 2+(v4) (v7) N (v4)

(v4)

H O

(v3)

(v4)

O– Cl O OO

(v4) Ru 2+(v4) N (v4) (v6) N (v4)

Rx-ID: 26518044 View in Reaxys 285/804 Yield

Conditions & References

>99

in water, Kinetics, 25°C, pH 2.0, 3 h, reaction monitored by UV-spectroscopy;; organic product extracted with pentane, complex identified by UV-spectroscopy, organic product by g.c.-m.s. Marmion, Mary E.; Takeuchi, Kenneth J.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1988); p. 2385 - 2392 ; (from Gmelin) View in Reaxys

HO O

Rx-ID: 1846534 View in Reaxys 286/804 Yield

Conditions & References With water, hydrogen iodide, acetic acid, PdCl2(tri(2-thienyl)phosphine)2 in various solvent(s), T= 160 °C , Product distribution Gol'dfarb, Ya. L.; Pirozhkov, S. D.; Litvinov, V. P.; Dudinov, A. A.; Buiya, M. A.; Lapidus, A. L.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 10; (1987); p. 2080 - 2083; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1987); p. 2245 - 2248 View in Reaxys O O

HO O

Rx-ID: 1978374 View in Reaxys 287/804 Yield

Conditions & References With potassium permanganate, (benzyl)-tri-(butyl)-ammonium chloride in water, benzene, Time= 48h, Ambient temperature, Yield given. Yields of byproduct given Lehmann, Jochen; Marquardt, Norbert; Synthesis; nb. 12; (1987); p. 1064 - 1067 View in Reaxys

Rx-ID: 2897241 View in Reaxys 288/804 Yield 85 %

Conditions & References With dihydridotetrakis(triphenylphosphine)ruthenium(II), water, 4-phenylbut-3-en-2-one in ethylene glycol dimethyl ether, Time= 24h, T= 180 °C , in the absence of hydrogen acceptor (benzalacetone); other aldehydes, Product distribution, Mechanism Murahashi, Shun-Ichi; Naota, Takeshi; Ito, Keiichiro; Maeda, Yoshihiro; Taki, Hiroshi; Journal of Organic Chemistry; vol. 52; nb. 19; (1987); p. 4319 - 4327 View in Reaxys

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N O

Rx-ID: 3738972 View in Reaxys 289/804 Yield

Conditions & References With tetraethyl ammonium fluoride, electrolysis, Yield given. Yields of byproduct given Becker, James Y.; Zinger, Baruch; Yatziv, Shimon; Journal of Organic Chemistry; vol. 52; nb. 13; (1987); p. 2783 - 2789 View in Reaxys

N O

Rx-ID: 3792159 View in Reaxys 290/804 Yield

Conditions & References With tetraethyl ammonium fluoride in acetonitrile, electrolysis, Yield given. Yields of byproduct given Becker, James Y.; Zinger, Baruch; Yatziv, Shimon; Journal of Organic Chemistry; vol. 52; nb. 13; (1987); p. 2783 - 2789 View in Reaxys

O O

Rx-ID: 1860393 View in Reaxys 291/804 Yield

Conditions & References

19 %, 9 %, With oxygen, anhydrous cobalt diacetate, T= 90 °C , p= 750.06Torr , other oxygen pressure, Mechanism, Rate con2 %, 4 % stant Vcelak, Jaroslav; Klimova, Miroslava; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 51; nb. 4; (1986); p. 847 - 866 View in Reaxys

HO OH O

Rx-ID: 1860400 View in Reaxys 292/804 Yield

Conditions & References

14 %, 8 %, With oxygen, anhydrous cobalt diacetate, T= 90 °C , p= 750.06Torr , other oxygen pressure, Mechanism, Rate con2% stant Vcelak, Jaroslav; Klimova, Miroslava; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 51; nb. 4; (1986); p. 847 - 866 View in Reaxys

HO O

Rx-ID: 1950185 View in Reaxys 293/804 Yield

Conditions & References With water, β-diketone hydrolase, Time= 15h, T= 30 °C , in phosphate buffer at pH 7.0; substrate specifity of catalyst, Product distribution

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Sakai, Kiyofumi; Hamada, Nobutake; Watanabe, Yasuto; Agricultural and Biological Chemistry; vol. 50; nb. 4; (1986); p. 989 - 996 View in Reaxys

HO O

Rx-ID: 2526718 View in Reaxys 294/804 Yield

Conditions & References

33 %, 9 %, With oxygen, anhydrous cobalt diacetate, T= 90 °C , p= 750.06Torr , other oxygen pressure, Mechanism, Rate con22 %, 12 stant % Vcelak, Jaroslav; Klimova, Miroslava; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 51; nb. 4; (1986); p. 847 - 866 View in Reaxys

O O

Rx-ID: 2526719 View in Reaxys 295/804 Yield

Conditions & References

14 %, 33 With oxygen, anhydrous cobalt diacetate, T= 90 °C , p= 750.06Torr , other oxygen pressure, Mechanism, Rate con%, 6 %, 26 stant %, 12 %, 6 Vcelak, Jaroslav; Klimova, Miroslava; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communica% tions; vol. 51; nb. 4; (1986); p. 847 - 866 View in Reaxys

HO OH O

Rx-ID: 2526721 View in Reaxys 296/804 Yield

Conditions & References

5.5 %, 3.5 %, 5 %, 7 %, 3 %, 73.5 %

With oxygen, anhydrous cobalt diacetate, T= 90 °C , p= 750.06Torr , other oxygen pressure, Mechanism, Rate constant Vcelak, Jaroslav; Klimova, Miroslava; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 51; nb. 4; (1986); p. 847 - 866 View in Reaxys

Rx-ID: 2527561 View in Reaxys 297/804

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Yield

Conditions & References

46 %, 6 %, With oxygen, anhydrous cobalt diacetate, T= 90 °C , p= 750.06Torr , other pressure, Mechanism, Rate constant 2 %, 10 % Vcelak, Jaroslav; Klimova, Miroslava; Chvalovsky, Vaclav; Collection of Czechoslovak Chemical Communications; vol. 51; nb. 4; (1986); p. 847 - 866 View in Reaxys

H N

Rx-ID: 3421542 View in Reaxys 298/804 Yield

Conditions & References With water in tert-butyl alcohol, T= 25 °C , kinetic solvent effect; hydrolysis, Rate constant Blokzijl, Wilfried; Jager, Jan; Engberts, Jan B. F. N.; Blandamer, Michael J.; Journal of the American Chemical Society; vol. 108; nb. 20; (1986); p. 6411 - 6413 View in Reaxys O

O C

Rx-ID: 3942790 View in Reaxys 299/804 Yield

Conditions & References With tetracarbonylbis(μ-chloro)dirhodium(I), hydrogen, hydrocarbonylation with various catalysts, Product distribution Bitsi, Gustave; Kheradmand, Houchang; Jenner, Gerard; Journal of Organometallic Chemistry; vol. 310; (1986); p. 115 - 120 View in Reaxys O

O C

OH O

Rx-ID: 3942791 View in Reaxys 300/804 Yield

Conditions & References

42 % Chromat., 30 % Chromat.

With hydrogen, anhydrous cobalt diacetate, Time= 5h, T= 180 °C , p= 150012Torr Bitsi, Gustave; Kheradmand, Houchang; Jenner, Gerard; Journal of Organometallic Chemistry; vol. 310; (1986); p. 115 - 120 View in Reaxys O

O C

Rx-ID: 3942792 View in Reaxys 301/804 Yield

Conditions & References With hydrogen, anhydrous cobalt diacetate, Time= 5h, T= 180 °C , p= 150012Torr Bitsi, Gustave; Kheradmand, Houchang; Jenner, Gerard; Journal of Organometallic Chemistry; vol. 310; (1986); p. 115 - 120 View in Reaxys

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O C

Rx-ID: 3942795 View in Reaxys 302/804 Yield

Conditions & References

38 % Chromat., 7 % Chromat., 14 % Chromat.

O C

Rx-ID: 3942797 View in Reaxys 303/804 Yield

Conditions & References

17 % Chromat., 3 % Chromat., 10 % Chromat.

With Rhodium trichloride, carbon monoxide, hydrogen, Time= 5h, T= 230 °C , p= 150012Torr Bitsi, Gustave; Kheradmand, Houchang; Jenner, Gerard; Journal of Organometallic Chemistry; vol. 310; (1986); p. 115 - 120 View in Reaxys

O C

OH O

Rx-ID: 3942798 View in Reaxys 304/804 Yield

Conditions & References

17 % Chromat., 10 % Chromat., 3 % Chromat.

With Rhodium trichloride, hydrogen, Time= 5h, T= 230 °C , p= 150012Torr Bitsi, Gustave; Kheradmand, Houchang; Jenner, Gerard; Journal of Organometallic Chemistry; vol. 310; (1986); p. 115 - 120 View in Reaxys

HO O

Rx-ID: 3942800 View in Reaxys 305/804 Yield

Conditions & References

38 % Chromat.

With tetracarbonylbis(μ-chloro)dirhodium(I), carbon monoxide, hydrogen, Time= 5h, T= 180 °C , p= 150012Torr Bitsi, Gustave; Kheradmand, Houchang; Jenner, Gerard; Journal of Organometallic Chemistry; vol. 310; (1986); p. 115 - 120 View in Reaxys O

O O

Rx-ID: 3951007 View in Reaxys 306/804 Yield 18 % Chromat., 5 % Chromat., 48 % Chromat.

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O O

Rx-ID: 3951008 View in Reaxys 307/804 Yield

O O

Rx-ID: 3951009 View in Reaxys 308/804 Yield

Conditions & References

16 % Chromat., 29 % Chromat.

With tetracarbonylbis(μ-chloro)dirhodium(I), hydrogen, Time= 5h, T= 180 °C , p= 150012Torr Bitsi, Gustave; Kheradmand, Houchang; Jenner, Gerard; Journal of Organometallic Chemistry; vol. 310; (1986); p. 115 - 120 View in Reaxys

Rx-ID: 1603602 View in Reaxys 309/804 Yield

Conditions & References With [RhCl(η2:η2-cycloocta-1,5-diene)]2, T= 80 - 250 °C Deklewa, Thomas W.; Forster, Denis; Journal of the American Chemical Society; vol. 107; nb. 12; (1985); p. 3565 - 3567 View in Reaxys With [RhCl(η2:η2-cycloocta-1,5-diene)]2, T= 100 - 170 °C , various temperatures, Thermodynamic data, Rate constant Deklewa, Thomas W.; Forster, Denis; Journal of the American Chemical Society; vol. 107; nb. 12; (1985); p. 3565 - 3567 View in Reaxys O O

OH OH

HO O

Rx-ID: 1869487 View in Reaxys 310/804 Yield

Conditions & References With emulsified substrate, water, acetic acid in various solvent(s), T= 30 °C , pH 4.20, Rate constant, Product distribution Diez, Tomas A.; Mata-Segreda, Julio F.; Phytochemistry (Elsevier); vol. 24; nb. 12; (1985); p. 3047 - 3048 View in Reaxys

O O

HO O

Rx-ID: 1944060 View in Reaxys 311/804

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Yield

HO HO

Rx-ID: 1945667 View in Reaxys 312/804 Yield

Cl O

H N

Cl O

NH 2

Rx-ID: 2123978 View in Reaxys 313/804 Yield

Conditions & References

45 %, 15 With sodium peroxodisulphate, copper dichloride in water, Time= 7.5h, T= 70 °C , Product distribution %, 7 %, 15 Troyanskii, E. I.; Ioffe, V. A.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical %, 5 %, 5 Science (English Translation); vol. 34; nb. 8; (1985); p. 1656 - 1661; Izvestiya Akademii Nauk SSSR, Seriya Khimi% cheskaya; nb. 8; (1985); p. 1808 - 1814 View in Reaxys

H N

N H

O Cl

HO O

Rx-ID: 2878182 View in Reaxys 314/804 Yield

Conditions & References

24 % Turnov., 18 % Turnov., 10 % Turnov., 8 % Turnov.

With sodium peroxodisulphate, copper dichloride in water, Time= 7.5h, T= 70 - 80 °C , Product distribution Troyanskii, E. I.; Ioffe, V. A.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; nb. 8; (1985); p. 1656 - 1661; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 8; (1985); p. 1808 - 1814 View in Reaxys

HO O

Rx-ID: 2894605 View in Reaxys 315/804 Yield

Conditions & References With sodium hydroxide, sodium bromite, sodium bromide in water, Time= 1h, Ambient temperature Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Fujisaki, Shizuo; Synthesis; nb. 6/7; (1985); p. 674 675 View in Reaxys

HO O

Rx-ID: 2896411 View in Reaxys 316/804

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Yield

Conditions & References in toluene, Time= 2h, T= 110 °C , Yield given. Further byproducts given. Yields of byproduct given Alferov, V. A.; Chikinova, N. V.; Vyshinskii, N. N.; Makin, G. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 12; (1985); p. 2730 - 2735,2428 - 2433 View in Reaxys in toluene, Time= 2h, T= 110 °C , Mechanism Alferov, V. A.; Chikinova, N. V.; Vyshinskii, N. N.; Makin, G. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 12; (1985); p. 2730 - 2735,2428 - 2433 View in Reaxys

OH C

Rx-ID: 3516023 View in Reaxys 317/804 Yield

Conditions & References With hydrogen iodide, rhodium in water, acetic acid, T= 170 °C , p= 18316Torr , various temperatures and pressures, various HI concentrations, kinetic isotop effect with D labeled compounds, Rate constant, Product distribution Dekleva, Thomas W.; Forster, Denis; Journal of the American Chemical Society; vol. 107; nb. 12; (1985); p. 3568 3572 View in Reaxys

O HO

Rx-ID: 3927290 View in Reaxys 318/804 Yield

Conditions & References With hydrogen, aluminum oxide, T= 276.9 °C , p= 0.4Torr Templeton; Weinberg; Journal of the American Chemical Society; vol. 107; nb. 3; (1985); p. 544 - 551 View in Reaxys

HO O

Rx-ID: 645849 View in Reaxys 319/804 Yield

Conditions & References

0.8 %, 90.5 %

With oxygen in neat (no solvent), T= 30 - 40 °C , with solvent (benzene) Blanshtein, I. B.; Del'nik, V. B.; Katsnel'son, M. G.; J. Appl. Chem. USSR (Engl. Transl.); vol. 54; nb. 2; (1981); p. 469 - 470,359 - 360 View in Reaxys With oxygen, palladium diacetate, tetrabutyl-ammonium chloride in chlorobenzene, T= 10 °C , other catalysts, Rate constant, Product distribution Onsager, Olav-T.; Swensen, Hanne C. A.; Johansen, Jon E.; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 38; nb. 7; (1984); p. 567 - 572 View in Reaxys With tetrachloromethane, oxygen, ozone, T= -20 - -10 °C Fischer; Duell; Volz; Justus Liebigs Annalen der Chemie; vol. 486; (1931); p. 87,90,92,93 View in Reaxys

HO OH

Rx-ID: 1860271 View in Reaxys 320/804

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Yield

Conditions & References

16 %, 45 %

With sodium peroxodisulphate, silver nitrate in water, Time= 3h, T= 60 °C Ogibin, Yu. N.; Velibekova, D. S.; Katsin, M. I.; Troyanskii, E. I.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 8; (1981); p. 1511 - 1515; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 30; nb. 8; (1981); p. 1842 - 1846 View in Reaxys

45 %, 16 %

With sodium peroxodisulphate, silver nitrate in water, Time= 5h, T= 60 °C , competition with tert-butanol, Rate constant Ogibin, Yu. N.; Velibekova, D. S.; Katsin, M. I.; Troyanskii, E. I.; Nikishin, G. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 8; (1981); p. 1511 - 1515; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 30; nb. 8; (1981); p. 1842 - 1846 View in Reaxys

45 %, 16 %

39 % Turn- With sodium peroxodisulphate in water, Time= 6h, T= 60 °C ov., 25 % Ogibin, Yu.N.; Makhova, I.V.; Gorozhankin, S.K.; Nikishin, G.I.; Bulletin of the Academy of Sciences of the USSR, Turnov. Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2099 - 2104; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2300 - 2305 View in Reaxys 39 % Turn- With sodium peroxodisulphate in water, Time= 6h, T= 60 °C , other alkanal cyanohydrins, Ag(1+) presence, other ov., 25 % temperature, Product distribution, Mechanism Turnov. Ogibin, Yu.N.; Makhova, I.V.; Gorozhankin, S.K.; Nikishin, G.I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2099 - 2104; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2300 - 2305 View in Reaxys 25 % Turn- With sodium peroxodisulphate in water, Time= 6h, T= 60 °C ov., 39 % Ogibin, Yu.N.; Makhova, I.V.; Gorozhankin, S.K.; Nikishin, G.I.; Bulletin of the Academy of Sciences of the USSR, Turnov. Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2099 - 2104; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2300 - 2305 View in Reaxys

Rx-ID: 1896455 View in Reaxys 321/804 Yield

Conditions & References

12.5 %

With Al-anode in N,N-dimethyl-formamide, T= 20 °C , electrocarboxylation Silvestri, Giuseppe; Gambino, Salvatore; Filardo, Giuseppe; Gulotta, Antonio; Angewandte Chemie; vol. 96; nb. 12; (1984); p. 978 - 979 View in Reaxys

HO O

Rx-ID: 1933013 View in Reaxys 322/804 Yield

Conditions & References With water, Amberlite IR-120, T= 60 °C , the effect of temperature was studied, Equilibrium constant

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Ewady, Y.A.El; Wakil, A.M.El; Nahas, M.R.El; Moussa, M.M.H.; Journal of the Indian Chemical Society; vol. 61; (1984); p. 517 - 519 View in Reaxys

HO O

Rx-ID: 3533477 View in Reaxys 323/804 Yield

Conditions & References With sulfuric acid, T= 80 °C , Product distribution, Kinetics, Equilibrium constant Chubarov; Danov; Logutov; Obmelyukhina; Journal of applied chemistry of the USSR; vol. 57; nb. 6 pt 2; (1984); p. 1229 - 1233 View in Reaxys

Rx-ID: 4086230 View in Reaxys 324/804 Yield

Conditions & References With potassium hydroxide, potassium meta-periodate, T= 49.9 °C , Rate constant, Mechanism Swarnalakshmi, N.; Uma, V.; Sethuram, B.; Navaneeth Rao, T.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 23; nb. 8; (1984); p. 646 - 649 View in Reaxys

iPrCOOH O

Rx-ID: 7078974 View in Reaxys 325/804 Yield

Conditions & References With water, hydrogen, palladium diacetate, triphenylphosphine in trifluoroacetic acid, T= 70 °C , p= 760Torr , var. of temp., conc. of H2O, Product distribution, Kinetics, Mechanism Zudin, Vladimir N.; Il'inich, Galina N.; Likholobov, Vladimir A.; Yermakov, Yurii I.; Journal of the Chemical Society, Chemical Communications; nb. 8; (1984); p. 545 - 546 View in Reaxys O

H N

Rx-ID: 1934523 View in Reaxys 326/804 Yield

Conditions & References

2 % Chromat., 90 % Chromat.

With sodium peroxodisulphate, copper dichloride in water, Time= 10h, T= 85 - 90 °C Nikishin, Gennady I.; Svitanko, Igor V.; Troyansky, Emmanuil I.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 595 - 602 View in Reaxys O

H N

HO O

Rx-ID: 1939623 View in Reaxys 327/804

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Yield

Conditions & References

6 % Chromat., 83 % Chromat.

O O

Rx-ID: 1514444 View in Reaxys 328/804 Yield

Conditions & References

26.3 %, 25.2 %, 15.8 %, 14.0 %, 10.8 %

Time= 6h, T= 90 °C , Product distribution Yur'ev, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 18; nb. 10; (1982); p. 1775 - 1781; Zhurnal Organicheskoi Khimii; vol. 18; nb. 10; (1982); p. 2021 - 2028 View in Reaxys

O O

O H

HO O

Rx-ID: 1514445 View in Reaxys 329/804 Yield

Conditions & References

21.0 %, 19.8 %, 20.2 %, 19.3 %, 1.1 %

in acetic acid, Time= 6h, T= 90 °C , other solvents, other temperature, ΔS (excit.), ΔG (excit.), ΔH (excit.), Product distribution, Thermodynamic data, Rate constant Yur'ev, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 18; nb. 10; (1982); p. 1775 - 1781; Zhurnal Organicheskoi Khimii; vol. 18; nb. 10; (1982); p. 2021 - 2028 View in Reaxys

Rx-ID: 1905257 View in Reaxys 330/804 Yield

Conditions & References in dichloromethane, Time= 18h, T= 60 - 70 °C , Irradiation, Yield given Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 16; (1982); p. 2525 - 2538 View in Reaxys O– O

Na +

HO O

Rx-ID: 2475407 View in Reaxys 331/804 Yield

Conditions & References

96 %

With Ca(OCl)2, acetic acid in dichloromethane, water, acetonitrile, Time= 3h, Ambient temperature Nwaukwa, Stephen O.; Keehn, Philip M.; Tetrahedron Letters; vol. 23; nb. 31; (1982); p. 3135 - 3138 View in Reaxys

HO O

Rx-ID: 3032498 View in Reaxys 332/804 Yield 84 %

Conditions & References With hydrogenchloride in water, Time= 5h, Heating Costisella, Burkhard; Gross, Hans; Tetrahedron; vol. 38; nb. 1; (1982); p. 139 - 145

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View in Reaxys O C

HO O

Rx-ID: 3537819 View in Reaxys 333/804 Yield

Conditions & References With water, hydrogen iodide, TsVK-2, palladium, Time= 2h, T= 130 °C , p= 60800Torr , further temperature (110, 150, 170, 200 deg C); effect of the concentration of HI; effect of the pressure of CO, Product distribution Lapidus, A. L.; Pirozhkov, S. D.; Vellekov, A.; Garanin, V. I.; Slyunyaev, P. I.; Minachev, Kh. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 10; (1982); p. 2027 - 2030; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1982); p. 2304 - 2306 View in Reaxys O O

Rx-ID: 3541785 View in Reaxys 334/804 Yield

Conditions & References

92 %, 19 %

With oxygen, methylene blue in pyridine, acetonitrile, Time= 2h, Irradiation Ando, Wataru; Miyazaki, Hajime; Akasaka, Takeshi; Tetrahedron Letters; vol. 23; nb. 26; (1982); p. 2655 - 2656 View in Reaxys

19 %, 92 %

OH O

Rx-ID: 3541805 View in Reaxys 335/804 Yield 66 %

Conditions & References With diazofluorenone, methylene blue in pyridine, acetonitrile, Time= 1.33333h, Irradiation Ando, Wataru; Miyazaki, Hajime; Akasaka, Takeshi; Tetrahedron Letters; vol. 23; nb. 11; (1982); p. 1197 - 1200 View in Reaxys

HO OH

OH O

racemate

Rx-ID: 3914126 View in Reaxys 336/804 Yield

Conditions & References Irradiation, different light sources, Product distribution Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 2; (1982); p. 245 - 255 View in Reaxys Time= 18h, T= 60 - 70 °C , Irradiation, Hg high pressure lamp, Yield given. Yields of byproduct given Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 2; (1982); p. 245 - 255

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View in Reaxys OH HO OH O

Rx-ID: 3914127 View in Reaxys 337/804 Yield

Conditions & References Irradiation, Yield given. Yields of byproduct given Balsells, R. Erra; Frasca, A. R.; Tetrahedron; vol. 38; nb. 16; (1982); p. 2525 - 2538 View in Reaxys

caprylic -, nonaoic -, capric acid, different ketones an gamma lactones

Rx-ID: 7070830 View in Reaxys 338/804 Yield

Conditions & References With oxygen, Time= 0.25h, T= 180 °C , p= 12920Torr , Product distribution Imre, L.; Danoczy, E.; Jalsovszky, G.; Holly S.; Journal of Molecular Structure; vol. 79; (1982); p. 35 - 38 View in Reaxys

O OH

isopropyl iodide O

Rx-ID: 7079241 View in Reaxys 339/804 Yield

Conditions & References With water, hydrogen iodide, TsVK-2, palladium, Time= 2h, T= 150 °C , p= 60800Torr , further temperature (170, 200 deg C), Product distribution Lapidus, A. L.; Pirozhkov, S. D.; Vellekov, A.; Garanin, V. I.; Slyunyaev, P. I.; Minachev, Kh. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 31; nb. 10; (1982); p. 2027 - 2030; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1982); p. 2304 - 2306 View in Reaxys

HO O

Rx-ID: 25059935 View in Reaxys 340/804 Yield 85%

Conditions & References 12 : 4-(3-trifluoromethylphenyl)-7-methoxy-1-tetralone reduction of the propionate ester to the propanol (93percent) tosylation (81percent), conversion to the butyronitrile (67percent) and hydrolysis to the butanoic acid (85percent), which was obtained as a pale yellow oil. Patent; Beecham Group Limited; US4322370; (1982); (A1) English View in Reaxys

O O

HO OH O

Rx-ID: 1522653 View in Reaxys 341/804

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Yield

Conditions & References

82.3 %, 1.0 %, 1.0 %, 1.2 %, 4.8 %

With hydrogen, 5 platinum on alumina, T= 250 °C , p= 152000Torr , var. catalysts, Product distribution Timofeev, A. F.; Shevchenko, V. S.; Tereshchenko, F. G.; J. Appl. Chem. USSR (Engl. Transl.); vol. 54; nb. 2; (1981); p. 335 - 338,225 - 228 View in Reaxys

HO O

Rx-ID: 1850337 View in Reaxys 342/804 Yield

Conditions & References

71 %

With iodosylbenzene, tris(triphenylphosphine)ruthenium(II) chloride in dichloromethane, Time= 0.0833333h, Ambient temperature Mueller, Paul; Godoy, Jose; Helvetica Chimica Acta; vol. 64; nb. 8; (1981); p. 2531 - 2533 View in Reaxys

Rx-ID: 1857278 View in Reaxys 343/804 Yield

Conditions & References

5 %, 93 %

With benzyltriethylammonium permanganate in dichloromethane Schmidt, H.-Juergen; Schaefer, Hans J.; Angewandte Chemie; vol. 93; nb. 1; (1981); p. 124 - 125 View in Reaxys

HO O

Rx-ID: 1941676 View in Reaxys 344/804 Yield

Conditions & References With ozone, Time= 6h, T= 20 °C , Yield given. Further byproducts given. Yields of byproduct given Korotkova, N. P.; Syroezhko, A. M.; Proskuryakov, V. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 54; nb. 4; (1981); p. 885 - 890,726 - 730 View in Reaxys

HO O

Rx-ID: 1942264 View in Reaxys 345/804 Yield

Conditions & References With ozone, Time= 2h, T= 40 °C , Yield given. Further byproducts given. Yields of byproduct given Korotkova, N. P.; Syroezhko, A. M.; Proskuryakov, V. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 54; nb. 4; (1981); p. 885 - 890,726 - 730 View in Reaxys With ozone, Time= 5h, T= 40 °C , Yield given. Further byproducts given. Yields of byproduct given Korotkova, N. P.; Syroezhko, A. M.; Proskuryakov, V. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 54; nb. 4; (1981); p. 885 - 890,726 - 730 View in Reaxys

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With ozone, Time= 2h, T= 80 °C , Yield given. Further byproducts given. Yields of byproduct given Korotkova, N. P.; Syroezhko, A. M.; Proskuryakov, V. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 54; nb. 4; (1981); p. 885 - 890,726 - 730 View in Reaxys With ozone, Time= 5h, T= 40 °C , other time, other temperature, Mechanism, Product distribution, Rate constant Korotkova, N. P.; Syroezhko, A. M.; Proskuryakov, V. A.; J. Appl. Chem. USSR (Engl. Transl.); vol. 54; nb. 4; (1981); p. 885 - 890,726 - 730 View in Reaxys H N N H

O O

HO O

Rx-ID: 2878183 View in Reaxys 346/804 Yield

Conditions & References

14 %, 30 %, 44 %

With benzyltriethylammonium permanganate in dichloromethane Schmidt, H.-Juergen; Schaefer, Hans J.; Angewandte Chemie; vol. 93; nb. 1; (1981); p. 124 - 125 View in Reaxys

44 %, 30 %, 14 %

With benzyltriethylammonium permanganate in dichloromethane Schmidt, H.-Juergen; Schaefer, Hans J.; Angewandte Chemie; vol. 93; nb. 1; (1981); p. 124 - 125 View in Reaxys

HO O

Rx-ID: 2881323 View in Reaxys 347/804 Yield

Conditions & References With hydrogen, tri-ruthenium(0)dodecacarbonyl, methyl iodide, T= 220 °C , p= 205200Torr , var. of catalyst, promotor, 13C-labelled, Product distribution, Mechanism Knifton, John F.; Journal of the Chemical Society, Chemical Communications; nb. 2; (1981); p. 41 - 43 View in Reaxys

HO O

Rx-ID: 2897821 View in Reaxys 348/804 Yield

Conditions & References

69 % Turn- With hydrogen, ruthenium(IV) oxide, methyl iodide, T= 220 °C , p= 205200Torr ov. Knifton, John F.; Journal of the Chemical Society, Chemical Communications; nb. 2; (1981); p. 41 - 43 View in Reaxys O

O O O

HO OH

resinous polyester

Rx-ID: 5744641 View in Reaxys 349/804 Yield 56.8 %, 1.4 %, 0.4

Conditions & References With hydrogen, 5 platinum on alumina in various solvent(s), T= 250 °C , p= 152000Torr , var. catalysts, Product distribution

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%, 0.9 %, 3.7 %

Timofeev, A. F.; Shevchenko, V. S.; Tereshchenko, F. G.; J. Appl. Chem. USSR (Engl. Transl.); vol. 54; nb. 2; (1981); p. 335 - 338,225 - 228 View in Reaxys

O O

O OH

butyraldehyde O

Rx-ID: 7070365 View in Reaxys 350/804 Yield

Conditions & References With dicobalt octacarbonyl, water, 1,2-bis-(diphenylphosphino)ethane in 1,4-dioxane, var. CO pressure, var. temperatures, var. H2O concentration, var. times, var. phosphines, var. H2 conc., var. pyridine conc., Product distribution Murata, Kazuhisa; Matsuda, Akio; Bulletin of the Chemical Society of Japan; vol. 54; nb. 1; (1981); p. 245 - 248 View in Reaxys

Na + O–

Rx-ID: 25051662 View in Reaxys 351/804 Yield

Conditions & References 2 : EXAMPLE 2 EXAMPLE 2 Carbon dioxide at 6200+-200 psig (423+-13.6 Atm, 42747*103 +-1379*103 Pag) at 77°+-2° C. was used to extract butyric acid from 15 ml of aqueous 0.5 M sodium butyrate. The concentration of butyrate in the aqueous phase dropped by about 19percent. About 21percent of the total butyrate was recovered as butyric acid in bomb 32, trap 33 and trap 34. The pH of the sodium butyrate solution dropped from 10.1 to 9.2. Patent; E. I. Du Pont de Nemours and Company; US4250331; (1981); (A1) English View in Reaxys 3 : EXAMPLE 3 EXAMPLE 3 Carbon dioxide at 2300+-200 psig (157.5+-13.6 Atm, 15856*103 +-1379*103 Pag) and 52°+-2° C. were used to extract butyric acid from 80 ml of aqueous 0.5 M sodium butyrate (bomb 31 was a 400 ml bomb, bomb 32 was a 75 ml bomb). About 4percent of the butyrate was recovered as butyric acid in bomb 32 and trap 34. The final density of the carbon dioxide was estimated to be about 0.8 that of the original density. Patent; E. I. Du Pont de Nemours and Company; US4250331; (1981); (A1) English View in Reaxys

Na + O–

Rx-ID: 25051663 View in Reaxys 352/804 Yield

Conditions & References 11 : EXAMPLE 11 EXAMPLE 11 Carbon dioxide at 2400+-200 psig (164+-13.6 Atm, 16547*103 +-1379*103 Pag) and 48°+-2° C. was used to extract butyric acid and hexanoic acid from 15 ml of an aqueous solution of 0.125 M sodium butyrate and 0.123 M sodium hexanoate, pH 9.6. The concentrations of sodium butyrate and sodium hexanoate in the aqueous phase were reduced by about 19percent and 53percent respectively. About 12percent of the sodium butyrate and 24percent of the sodium hexanoate were recovered as butyric acid and hexanoic acid respectively in bomb 32, trap 33 and trap 34.

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Patent; E. I. Du Pont de Nemours and Company; US4250331; (1981); (A1) English View in Reaxys

O O

Mg Br

Rx-ID: 1760269 View in Reaxys 353/804 Yield

Conditions & References

87 %

With copper(l) chloride, Time= 0.25h, T= 0 °C Sato, Toshio; Kawara, Tatsuo; Kawashima, Masatoshi; Fujisawa, Tamotsu; Chemistry Letters; (1980); p. 571 574 View in Reaxys

HO O

Rx-ID: 1848615 View in Reaxys 354/804 Yield

Conditions & References With RuO4 in tetrachloromethane, water, Time= 48h, Yield given. Yields of byproduct given Smith, Amos B.; Scarborough, Robert M.; Synthetic Communications; vol. 10; nb. 3; (1980); p. 205 - 212 View in Reaxys F O

HO O

Rx-ID: 2007952 View in Reaxys 355/804 Yield

Conditions & References

82 % Chromat., 18 % Chromat.

Product distribution Liotta, R.; Hoff, W. S.; Journal of Organic Chemistry; vol. 45; nb. 14; (1980); p. 2887 - 2890 View in Reaxys

O O

O HO

Rx-ID: 2034005 View in Reaxys 356/804 Yield

Conditions & References With oxygen in acetonitrile, Irradiation, other solvents (sensitizer: methylene blue, MB; rose bengal, RB; polymerbased rose bengal, p-RB), Yield given Frimer, Aryeh A.; Antebi, Abraham; Journal of Organic Chemistry; vol. 45; nb. 12; (1980); p. 2334 - 2340 View in Reaxys With oxygen in acetonitrile, Irradiation, other solvents (sensitizers: methylene blue, MB; rose bengal, RB; polymer based rose bengal, p-RB), Product distribution, Mechanism Frimer, Aryeh A.; Antebi, Abraham; Journal of Organic Chemistry; vol. 45; nb. 12; (1980); p. 2334 - 2340 View in Reaxys

O O

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Rx-ID: 2067769 View in Reaxys 357/804 Yield

Conditions & References With oxygen in acetonitrile, Irradiation, other solvents (sensitizers: methylene blue, MB; rose bengal, RB; polymerbased rose bengal, p-RB), Product distribution, Mechanism Frimer, Aryeh A.; Antebi, Abraham; Journal of Organic Chemistry; vol. 45; nb. 12; (1980); p. 2334 - 2340 View in Reaxys

Rx-ID: 2067770 View in Reaxys 358/804 Yield

Conditions & References With oxygen in acetonitrile, Irradiation, other solvents (sensitizer: methylene blue, MB; rose bengal, RB), Yield given Frimer, Aryeh A.; Antebi, Abraham; Journal of Organic Chemistry; vol. 45; nb. 12; (1980); p. 2334 - 2340 View in Reaxys

E O

Rx-ID: 2081518 View in Reaxys 359/804 Yield

Conditions & References With oxygen in acetonitrile, Irradiation, other solvents (sensitizers: methylene blue, MB; rose bengal, RB; polymer based rose bengal, p-RB), Product distribution, Mechanism Frimer, Aryeh A.; Antebi, Abraham; Journal of Organic Chemistry; vol. 45; nb. 12; (1980); p. 2334 - 2340 View in Reaxys O O

OH O

Rx-ID: 2527713 View in Reaxys 360/804 Yield

Conditions & References T= 90 °C , other temperatures: 70, 80, 85, 95, 96, 105, 113, 120 deg. C; presence of inhibitor: α-naphthol; kinetics, Rate constant, Product distribution, Mechanism Estrina, G. Ya.; Kuramshin, E. M.; Imashev, U. B.; Zlotskii, S. S.; Rakhmankulov, D. L.; Journal of Organic Chemistry USSR (English Translation); vol. 16; nb. 7; (1980); p. 1355 - 1359; Zhurnal Organicheskoi Khimii; vol. 16; nb. 7; (1980); p. 1598 - 1603

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View in Reaxys O H

Rx-ID: 2897200 View in Reaxys 361/804 Yield

Conditions & References

10.54 % Turnov., 0.67 % Turnov., 15.7 % Turnov.

With sodium n-butanolate in butan-1-ol, water removed with the aid of a Dean and Stark attachment, Further byproducts given Krut-skii, L. N.; Vanin, V. V.; Khisamutdinov, G. Kh.; Krut-skaya, L. V.; Lyubomilov, V. I.; J. Appl. Chem. USSR (Engl. Transl.); vol. 53; nb. 7; (1980); p. 1616 - 1619,1261 - 1264 View in Reaxys

O O

Rx-ID: 2919312 View in Reaxys 362/804 Yield

Conditions & References With copper powder in gas, Time= 4.16667E-05h, Irradiation, Structure of positively charged products of reaction., Product distribution Burnier, R. C.; Byrd, G. D.; Freiser, B. S.; Analytical Chemistry; vol. 52; nb. 11; (1980); p. 1641 - 1650 View in Reaxys O

Me2CuLi

Rx-ID: 6188391 View in Reaxys 363/804 Yield

Conditions & References

71 % Chromat.

in tetrahydrofuran, 1.) -30 deg C, 1 h, 2.) 0 deg C, 1 h Fujisawa, Tamotsu; Sato, Toshio; Kawara, Tatsuo; Kawashima, Masatoshi; Tetrahedron Letters; vol. 21; (1980); p. 2181 - 2184 View in Reaxys

O O

Me2CuMgBr

Rx-ID: 6188392 View in Reaxys 364/804 Yield

Conditions & References

89 % Chromat.

in tetrahydrofuran, 1.) -30 deg C, 1 h, 2.) 0 deg C, 1 h Fujisawa, Tamotsu; Sato, Toshio; Kawara, Tatsuo; Kawashima, Masatoshi; Tetrahedron Letters; vol. 21; (1980); p. 2181 - 2184 View in Reaxys

N O

HO O

Rx-ID: 25268212 View in Reaxys 365/804 Yield 90 %

Conditions & References VII : EXAMPLE VII EXAMPLE VII The procedure of Example VI was repeated except 11.0 grams (0.1 mole) of 4-octene was employed as starting material and 27.0 grams of solids composed of calcium nitrate and the calcium salt of the nitroketone were separated by filtration.

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Extraction and acidification provided 8.7 grams of nitrobutane (92 percent yield) and 7.9 grams of butanoic acid (90 percent yield). Patent; Texaco Inc.; US4013697; (1977); (A1) English View in Reaxys

(v3) (v3)

(v6)

(v3)

(v3) (v3) O O (v6)

(v3)

O (v5)

(v3)

O O

(v3)

(v5)

(v3)

(v7) Co (v7)Co

(v3)

Co (v5)(v7) O

(v3) O (v3)

Co O O (v3) O (v5) (v3)

(v3)

Rx-ID: 26594583 View in Reaxys 366/804 Yield

Conditions & References With H2 in benzene, High Pressure; hydrogenation at higher temp. and higher pressure; presence of phosphines, phosphites, arsines, stibines inhibits formation of butyric acid Sato, S.; Morishima, A.; Wakamatsu, H.; Nippon Kagaku Zasshi; vol. 91; (1970); p. 557 - 561; C.A.; vol. 73; (1970); p. 120030 View in Reaxys vol. Co: Org.Verb.2; 2.1.6, page 79 - 81 ; (from Gmelin) View in Reaxys O

N O

HO O

Rx-ID: 729519 View in Reaxys 367/804 Yield

Conditions & References Ferris; Journal of Organic Chemistry; vol. 24; (1959); p. 580 View in Reaxys

oxygen

N H

Rx-ID: 7066123 View in Reaxys 368/804 Yield

Conditions & References T= 25 °C , Geschwindigkeit der Reaktion mit UV-Licht auch nach Zusatz von tert-Butylhydroperoxid und von Di-tertbutylperoxid.Irradiation Stratford; ; vol. 144250; (1959); p. 4,8,12 View in Reaxys T= 34 °C , Geschwindigkeit der Reaktion mit UV-Licht auch nach Zusatz von tert-Butylhydroperoxid und von Di-tertbutylperoxid.Irradiation Stratford; ; vol. 144250; (1959); p. 4,8,12 View in Reaxys

oxygen

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N H

Rx-ID: 7066124 View in Reaxys 369/804 Yield

N HO

S OO

NH 2

Rx-ID: 7067036 View in Reaxys 370/804 Yield

Conditions & References Ferris; Journal of Organic Chemistry; vol. 24; (1959); p. 580 View in Reaxys

O O

Rx-ID: 175667 View in Reaxys 371/804 Yield

Conditions & References T= 86 °C , Pr. 5: Wasserstoff.Thermolysis Durham et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 332,334 View in Reaxys

Rx-ID: 188613 View in Reaxys 372/804 Yield

Conditions & References T= 25 °C , Hydrogenation Flitcroft; Skinner; Transactions of the Faraday Society; vol. 54; (1958); p. 47,50 View in Reaxys

OH O

H 2N 2

HO O

Rx-ID: 587051 View in Reaxys 373/804 Yield

Conditions & References With diethyl ether, n-heptane, T= 220 °C , p= 220652Torr Sacharkin; Gawrilenko; Doklady Akademii Nauk SSSR; vol. 118; (1958); p. 713; Doklady Chemistry; 118-123<1958>95 View in Reaxys

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aqueous sodium hypochlorite O O

OH H

Rx-ID: 6188426 View in Reaxys 374/804 Yield

Conditions & References Schaer; Helvetica Chimica Acta; vol. 41; (1958); p. 560,572 View in Reaxys

N O

H 2N

N O

H 2N 2

H N

propylamine nitrate

nitrogen

Rx-ID: 6219033 View in Reaxys 375/804 Yield

Conditions & References T= 0 °C Bachman; Michalowicz; Journal of Organic Chemistry; vol. 23; (1958); p. 1800 View in Reaxys

butaraldehyde

HO O

Rx-ID: 7066097 View in Reaxys 376/804 Yield

Conditions & References T= 86 °C , Pyrolysis Wurster et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 327,328,330,331 View in Reaxys

boron fluorid-adduct of dinitrogen tetraoxide

OH O

Rx-ID: 7066691 View in Reaxys 377/804 Yield

Conditions & References Bachman; Vogt; Journal of the American Chemical Society; vol. 80; (1958); p. 2987,2988 View in Reaxys

hydrogen

Rx-ID: 7078419 View in Reaxys 378/804 Yield

Conditions & References T= 86 °C , im UV-licht bereits bei 35grad; Produkt 5:Butylbutyrat.Irradiation Durham et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 332,334 View in Reaxys F

N O

F F

F HO

nitrogen monooxide

F O

Rx-ID: 7082412 View in Reaxys 379/804

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Yield

Conditions & References Merrow; Whitnack; Journal of Organic Chemistry; vol. 23; (1958); p. 1224 View in Reaxys

OH O

Rx-ID: 844850 View in Reaxys 380/804 Yield

Conditions & References With sodium hydroxide, nickel-chromium oxide, water, T= 120 °C Ljubomilov et al.; Zhurnal Obshchei Khimii; vol. 27; (1957); p. 2054;engl.Ausg.S.2108 View in Reaxys

methanol. NaOH-solution

HO O

Rx-ID: 6188428 View in Reaxys 381/804 Yield

Conditions & References House; Wasson; Journal of Organic Chemistry; vol. 22; (1957); p. 1157,1160 View in Reaxys

Rx-ID: 645580 View in Reaxys 382/804 Yield

Conditions & References T= 20 - 50 °C , auch nach Zusatz Kupfer(II)-, Mangan(II)-, Eisen(II)-, Kobalt(II)- und Nickel(II)-butyrat, Rate constant Vrbaski; Brihta; Arhiv za Kemiju; vol. 26; (1954); p. 267,272,275 View in Reaxys Brihta; Vrbaski; Croatica Chemica Acta; vol. 28; (1956); p. 19,20,21 View in Reaxys

NH 2

Rx-ID: 6684749 View in Reaxys 383/804 Yield

Conditions & References T= 220 °C , Pyrolysis Davidson; Karten; Journal of the American Chemical Society; vol. 78; (1956); p. 1066 View in Reaxys

E O

H 2N

H O

NH 2

aqueous NaOH-solution

palladium/charcoal

HO O

Rx-ID: 7066060 View in Reaxys 384/804 Yield

Conditions & References Pietra; Annali di Chimica (Rome, Italy); vol. 46; (1956); p. 477,480 View in Reaxys

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S S

S HO

sulfur

O O

Rx-ID: 7087358 View in Reaxys 385/804 Yield

Conditions & References Behringer; Grunwald; Justus Liebigs Annalen der Chemie; vol. 600; (1956); p. 23,31 View in Reaxys

carbon monoxide

Rx-ID: 6188375 View in Reaxys 386/804 Yield

Conditions & References With dicobalt octacarbonyl, water, bei hoher Temperatur und hohem Druck Patent; Eastman Kodak Co.; US2739169; (1952) View in Reaxys Patent; Eastman Kodak Co.; US2510105; (1948) View in Reaxys Patent; Eastman Kodak Co.; US2593440; (1948) View in Reaxys Ercoli; Chimica e l'Industria (Milan, Italy); vol. 37; (1955); p. 1029,1031 View in Reaxys With water, Ni(CO)4, bei hoher Temperatur und hohem Druck Patent; Eastman Kodak Co.; US2739169; (1952) View in Reaxys Patent; Eastman Kodak Co.; US2510105; (1948) View in Reaxys Patent; Eastman Kodak Co.; US2593440; (1948) View in Reaxys Ercoli; Chimica e l'Industria (Milan, Italy); vol. 37; (1955); p. 1029,1031 View in Reaxys

air

HO O

Rx-ID: 6208271 View in Reaxys 387/804 Yield

Conditions & References T= 130 °C , p= 2942.03Torr Pritzkow; Mueller; Justus Liebigs Annalen der Chemie; vol. 597; (1955); p. 167,170,178 View in Reaxys

air

HO O

Rx-ID: 7066155 View in Reaxys 388/804 Yield

Conditions & References T= 130 °C , p= 2942.03Torr Pritzkow; Mueller; Justus Liebigs Annalen der Chemie; vol. 597; (1955); p. 167,170,178 View in Reaxys

air

HO O

Rx-ID: 7067114 View in Reaxys 389/804

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Yield

Conditions & References T= 130 °C , p= 2942.03Torr , Produkt5: Hexansaeure Pritzkow; Mueller; Justus Liebigs Annalen der Chemie; vol. 597; (1955); p. 167,170,178 View in Reaxys

alkaline aqueous potassium permanganate

Na + O–

Rx-ID: 8264146 View in Reaxys 390/804 Yield

Conditions & References Neunhoeffer; Raths; Journal fuer Praktische Chemie (Leipzig); vol. <4>2; (1955); p. 84 View in Reaxys O

HO O

Rx-ID: 63487 View in Reaxys 391/804 Yield

Conditions & References Franzen; Chemische Berichte; vol. 87; (1954); p. 1219,1223 View in Reaxys

OH O

Rx-ID: 638806 View in Reaxys 392/804 Yield

Conditions & References Franzen; Chemische Berichte; vol. 87; (1954); p. 1219,1223 View in Reaxys

aqueous KOH-solution

lead (II)-oxide

HO O

Rx-ID: 6188389 View in Reaxys 393/804 Yield

Conditions & References T= 140 °C Danilow; Tichomipowa-Sidopowa; Zhurnal Obshchei Khimii; vol. 24; (1954); p. 458,464; engl. Ausg. S. 467, 472 View in Reaxys

2-propyl-valeric acid (?) O

Rx-ID: 7066109 View in Reaxys 394/804 Yield

Conditions & References Franzen; Chemische Berichte; vol. 87; (1954); p. 1219,1223 View in Reaxys Schlubach; Franzen; Justus Liebigs Annalen der Chemie; vol. 577; (1952); p. 60,61 View in Reaxys H

O O

N O

HO O

Rx-ID: 372539 View in Reaxys 395/804

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Yield

Conditions & References T= 120 °C , Zersetzung, Rate constant Brady; Sharawy; Journal of the Chemical Society; (1953); p. 4082,4083 View in Reaxys

carbon monoxide

Rx-ID: 6188374 View in Reaxys 396/804 Yield

Conditions & References With Ni(CO)4, T= 240 - 280 °C , p= 147102Torr Reppe et al.; Justus Liebigs Annalen der Chemie; vol. 582; (1953); p. 72,85 View in Reaxys

C O

Rx-ID: 6188433 View in Reaxys 397/804 Yield

Conditions & References With NiI2, nickel carbonyl, water, T= 230 °C , p= 36775.4Torr , Reagens4: Tetrahydrofuran Patent; du Pont de Nemours and Co.; US2448368; (1945) View in Reaxys Reppe; Kroeper; Justus Liebigs Annalen der Chemie; vol. 582; (1953); p. 54 View in Reaxys With tetrahydrofuran, NiI2, Ni(CO)4, T= 230 °C , p= 36775.4Torr Reppe; Kroeper; Justus Liebigs Annalen der Chemie; vol. 582; (1953); p. 54 View in Reaxys

nitrogen dioxide

HO O

Rx-ID: 7066084 View in Reaxys 398/804 Yield

Conditions & References Horner; Huebenett; Justus Liebigs Annalen der Chemie; vol. 579; (1953); p. 193,201 View in Reaxys

KMnO4

O O

O HO

OH O

Rx-ID: 7066099 View in Reaxys 399/804 Yield

Conditions & References der Aethylester reagiert Tsuchiya; Nippon Kagaku Kaishi; vol. 62; (1941); p. 552; ; (1943); p. 1384 View in Reaxys Tsuchiya; Nippon Kagaku Kaishi; vol. 63; (1942); p. 650; ; (1947); p. 3049 View in Reaxys Toyama; Yamamoto; ; vol. 2; (1953); p. 108,147; ; (1954); p. 1710 View in Reaxys

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C O

nickel carbonyl OH

Rx-ID: 7066172 View in Reaxys 400/804 Yield

Conditions & References T= 230 °C , p= 36775.4Torr , auch unter Zusatz von etwas NiI2, in Tetrahydrofuran Reppe; Kroeper; Justus Liebigs Annalen der Chemie; vol. 582; (1953); p. 54 View in Reaxys

air

Rx-ID: 7066162 View in Reaxys 401/804 Yield

Conditions & References T= 110 °C Sharp et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 1802 View in Reaxys T= 120 °C Sharp et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 1802 View in Reaxys

aqueous KOH-solution

oxygen

E HO

Z O O HO

OH O

Rx-ID: 7066080 View in Reaxys 402/804 Yield

Conditions & References T= 130 °C Treibs; Rothe; Chemische Berichte; vol. 84; (1951); p. 370,375 View in Reaxys

N H

H N

Rx-ID: 6188418 View in Reaxys 403/804 Yield

Conditions & References Smirnow; Schkljaruk; Zhurnal Obshchei Khimii; vol. 20; (1950); p. 334;engl.Ausg.S.355 View in Reaxys

NH 2

H N

HO O

Rx-ID: 6188419 View in Reaxys 404/804 Yield

Conditions & References Smirnow; Schkljaruk; Zhurnal Obshchei Khimii; vol. 20; (1950); p. 334;engl.Ausg.S.355 View in Reaxys

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aqueous potassium permanganate

N H

H N

Rx-ID: 6188420 View in Reaxys 405/804 Yield

Conditions & References Smirnow; Schkljaruk; Zhurnal Obshchei Khimii; vol. 20; (1950); p. 334;engl.Ausg.S.355 View in Reaxys

aqueous potassium permanganate

NH 2

H N

Rx-ID: 6188421 View in Reaxys 406/804 Yield

Conditions & References Smirnow; Schkljaruk; Zhurnal Obshchei Khimii; vol. 20; (1950); p. 334;engl.Ausg.S.355 View in Reaxys

chromium (VI)-oxide

N H

H N

Rx-ID: 6188422 View in Reaxys 407/804 Yield

Conditions & References Smirnow; Schkljaruk; Zhurnal Obshchei Khimii; vol. 20; (1950); p. 334;engl.Ausg.S.355 View in Reaxys

NH 2

chromium (VI)-oxide

H N

N H

HO O

Rx-ID: 6188423 View in Reaxys 408/804 Yield

Conditions & References Smirnow; Schkljaruk; Zhurnal Obshchei Khimii; vol. 20; (1950); p. 334;engl.Ausg.S.355 View in Reaxys

HO O

Rx-ID: 194051 View in Reaxys 409/804 Yield

Conditions & References bei der anaeroben Vergaerung im Gegenwart von Acetat oder Propionat durch Clostridium kluyveri oder ein daraus gewonnenes Fermentpraeparat Stadtman; Barker; Journal of Biological Chemistry; vol. 180; (1949); p. 1092 View in Reaxys Barker; Kamen; Bornstein; Proceedings of the National Academy of Sciences of the United States of America; vol. 31; (1945); p. 374,377; ; (1946); p. 1559 View in Reaxys Bornstein; Barker; Journal of Biological Chemistry; vol. 172; (1948); p. 659; ; vol. 55; (1948); p. 223 View in Reaxys bei der stillen elektrischen Entladung Loeb; Biochemische Zeitschrift; vol. 20; (1909); p. 134 View in Reaxys

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Rx-ID: 197440 View in Reaxys 410/804 Yield

Conditions & References Reduktion an Blei-Kathoden und an Quecksilber-Kathoden Dineen et al.; ; vol. 96; (1949); p. 226,229 View in Reaxys

OH P

Rx-ID: 241772 View in Reaxys 411/804 Yield

Conditions & References T= 26 °C , mit zellfreien Enzymloesung aus Clostridium kluyveri in Wasserstoffatmosphaere bei pH 8.1 Stadtman; Barker; Journal of Biological Chemistry; vol. 180; (1949); p. 1092 View in Reaxys

–O

Na +

Rx-ID: 636756 View in Reaxys 412/804 Yield

Conditions & References With hydrogen, bei der Einw. von Enzympraeparaten aus Clostridium kluyveri Stadtman; Barker; Journal of Biological Chemistry; vol. 180; (1949); p. 1092 View in Reaxys

HO O

Rx-ID: 648854 View in Reaxys 413/804 Yield

Conditions & References durch Einw. von Clostridium butylicum Cohen-Bazire et al.; ; vol. 142; p. 1221; ; (1949); p. 4331 View in Reaxys Aubel; Perdigon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 211; (1940); p. 440 View in Reaxys Davies; Stephenson; Biochemical Journal; vol. 35; (1941); p. 1328 View in Reaxys Osburn,Brown,Werkman; Iowa State College Journal of Science; vol. 12; (1938); p. 281; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 152 View in Reaxys Brown,Osburn,Werkman; ; vol. 36; (1937); p. 203; Chem. Zentralbl.; vol. 109; nb. II; (1938); p. 2601 View in Reaxys COHEN; COHEN-BAZIRE; Nature; vol. 162; nb. 4119; (1948); p. 578 - 578 View in Reaxys

Rx-ID: 839869 View in Reaxys 414/804 Yield

Conditions & References Nawrocki et al.; Industrial and Engineering Chemistry; vol. 41; (1949); p. 2607 View in Reaxys Patent; Shell Devel.Co.; US2452326; (1943)

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View in Reaxys Patent; Shell Devel.Co.; GB597029 View in Reaxys

–O

O Na +

acetyl phosphate

Rx-ID: 6188366 View in Reaxys 415/804 Yield

Conditions & References With hydrogen, bei der Einw. von Enzympraeparaten aus Clostridium kluyveri Stadtman; Barker; Journal of Biological Chemistry; vol. 180; (1949); p. 1092 View in Reaxys

propyne-(2)-carboxylic acid-(1)

Rx-ID: 6188403 View in Reaxys 416/804 Yield

Conditions & References With platinum(IV) oxide, methyl acetate Heilbron; Jones; Sondheimer; Journal of the Chemical Society; (1949); p. 606 View in Reaxys

KBrO3

HO O

Rx-ID: 6684741 View in Reaxys 417/804 Yield

Conditions & References in saurer Loesung (pH 2.5) von 40grad auf 100grad Farkas; Schaechter; Journal of the American Chemical Society; vol. 71; (1949); p. 2828; ; (1948); p. 7313 View in Reaxys

KMnO4

HO O

Rx-ID: 7066056 View in Reaxys 418/804 Yield

Conditions & References Hennion; Sheehan; Journal of the American Chemical Society; vol. 71; (1949); p. 1965 View in Reaxys

KMnO4

HO O

Rx-ID: 7066057 View in Reaxys 419/804 Yield

Conditions & References Hennion; Sheehan; Journal of the American Chemical Society; vol. 71; (1949); p. 1966 View in Reaxys

PtO2 O

HO O

Rx-ID: 7066067 View in Reaxys 420/804 Yield

Conditions & References Hydrogenation Heilbron; Jones; Sondheimer; Journal of the Chemical Society; (1949); p. 606 View in Reaxys

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aqueous KMnO4

HO O

Rx-ID: 7066096 View in Reaxys 421/804 Yield

Conditions & References 1-ethoxy-heptene-(3) Pudowik; Winokurowa; Zhurnal Obshchei Khimii; vol. 19; (1949); p. 1885/86; ; (1950); p. 1896 View in Reaxys

KMnO4

HO O

Rx-ID: 7066128 View in Reaxys 422/804 Yield

Conditions & References Jessafow; Zhurnal Obshchei Khimii; vol. 19; (1949); p. 1070; ; (1950); p. 1001 View in Reaxys

NH 2 O

Rx-ID: 7066141 View in Reaxys 423/804 Yield

Conditions & References durch Clostridium saccharobutyricum Cohen; Nisman; Cohen-Bazire; Bulletin de la Societe de Chimie Biologique; vol. 30; (1948); p. 109 View in Reaxys Rosenberg; Nisman; Biochimica et Biophysica Acta; vol. 3; (1949); p. 350,353 View in Reaxys Cohen et al.; Bulletin de la Societe de Chimie Biologique; vol. 29; (1947); p. 646; Bulletin de la Societe de Chimie Biologique; vol. 30; (1948); p. 110 View in Reaxys

O O

aqueous potassium permanganate solution

OH O

Rx-ID: 7920364 View in Reaxys 424/804 Yield

Conditions & References Djakonow; Zhurnal Obshchei Khimii; vol. 19; (1949); p. 2057,2063, 2065; ; (1950); p. 3915 View in Reaxys

aqueous potassium permanganate solution

O HO

OH O

Rx-ID: 7920365 View in Reaxys 425/804 Yield

Conditions & References Djakonow; Zhurnal Obshchei Khimii; vol. 19; (1949); p. 1897; ; (1950); p. 1916 View in Reaxys

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O HO

4-oxo-3-methyl-hexanoic acid (1) O

Rx-ID: 8264144 View in Reaxys 426/804 Yield

Conditions & References Ozonolyse Nasarow; Saretzkaja; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1949); p. 186; ; (1949); p. 6623 View in Reaxys O H

KMnO4

4-oxo-3-methyl-hexanoic acid (1) O

Rx-ID: 8264145 View in Reaxys 427/804 Yield

Conditions & References Nasarow; Saretzkaja; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1949); p. 186; ; (1949); p. 6623 View in Reaxys

NH 2

Rx-ID: 64510 View in Reaxys 428/804 Yield

Conditions & References bei der Vergaerung durch Clostridium propionicum Barker; Wiken; Archives of Biochemistry; vol. 17; (1948); p. 149 View in Reaxys Cardon; Barker; Archives of Biochemistry; vol. 12; (1947); p. 169 View in Reaxys

Na + O–

Rx-ID: 193418 View in Reaxys 429/804 Yield

Conditions & References Produkt5:Oenantsaeure ;Vergaerung durch Clostridium kluyveri Bornstein; Barker; Journal of Biological Chemistry; vol. 172; (1948); p. 659; ; vol. 55; (1948); p. 223 View in Reaxys

HO O

Rx-ID: 226505 View in Reaxys 430/804 Yield

Conditions & References bei der Ozonolyse Nasarow; Kuwarsina; Zhurnal Obshchei Khimii; vol. 18; (1948); p. 1329; ; (1949); p. 2161 View in Reaxys

O– Na + O

HO O

Rx-ID: 594350 View in Reaxys 431/804

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Yield

Conditions & References With sodium acetate, bei der Vergaerung durch Reinkulturen von Clostridium lactoacetophilum Bhat; Barker; ; vol. 56; (1948); p. 777; ; (1949); p. 2276 View in Reaxys With sodium acetate, bei der Vergaerung durch Rohkulturen von Clostridium lactoacetophilum Bhat; Barker; ; vol. 56; (1948); p. 777; ; (1949); p. 2276 View in Reaxys With sodium hydrogencarbonate, bei der Vergaerung durch Rohkulturen von Clostridium lactoacetophilum Bhat; Barker; ; vol. 56; (1948); p. 777; ; (1949); p. 2276 View in Reaxys With nickel oxide, water, hydrogen, T= 270 °C , p= 53200Torr , Reagens 4:Aluminiumoxyd Ipatjew; Rasuwajew; Chemische Berichte; vol. 59; (1926); p. 2032; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 58; (1926); p. 1347 View in Reaxys

–O

Co 2+

HO O

Rx-ID: 636834 View in Reaxys 432/804 Yield

Conditions & References T= 60 - 70 °C , Erwaermen mit Luft Patent; Eastman Kodak Co.; US2497889; (1948) View in Reaxys O

OH O

Rx-ID: 715354 View in Reaxys 433/804 Yield

Conditions & References Vergaerung durch Clostridium saccharobutyricum COHEN; COHEN-BAZIRE; Nature; vol. 162; nb. 4119; (1948); p. 578 - 578 View in Reaxys

Rx-ID: 793399 View in Reaxys 434/804 Yield

Conditions & References Bei der Vergaerung durch Clostridium saccharobutyricum oder Cl. acetobutylicum bei pH 7 COHEN; COHEN-BAZIRE; Nature; vol. 162; nb. 4119; (1948); p. 578 - 578 View in Reaxys O O

copper-chromium oxide

O O

HO O

Rx-ID: 6188415 View in Reaxys 435/804

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Yield

Conditions & References T= 250 °C , p= 220652Torr , Produkt 5: Tetrahydrofuran(?).Hydrogenation Adkins; Folkers; Journal of the American Chemical Society; vol. 53; (1931); p. 1096 View in Reaxys Patent; Roehm and Haas; US2091800; (1931) View in Reaxys Adkins; Billica; Journal of the American Chemical Society; vol. 70; (1948); p. 3121 View in Reaxys Wojcik; Adkins; Journal of the American Chemical Society; vol. 55; (1933); p. 4943 View in Reaxys O HO

air oxygen

Rx-ID: 7066052 View in Reaxys 436/804 Yield

Conditions & References Powell; Nielsen; Journal of the American Chemical Society; vol. 70; (1948); p. 3629 View in Reaxys

OH O

clostridium saccharobutyricum

HO O

Rx-ID: 7066127 View in Reaxys 437/804 Yield

Conditions & References COHEN; COHEN-BAZIRE; Nature; vol. 162; nb. 4119; (1948); p. 578 - 578 View in Reaxys

O H 2N

OH H

HO O

racemate

Rx-ID: 7066153 View in Reaxys 438/804 Yield

Conditions & References Clostridium propionicum bewirkt Abbau Barker; Wiken; Archives of Biochemistry; vol. 17; (1948); p. 149 View in Reaxys Cardon; Barker; Archives of Biochemistry; vol. 12; (1947); p. 169 View in Reaxys O

liver and kidneys-extract

Rx-ID: 7066165 View in Reaxys 439/804 Yield

Conditions & References Meister; Greenstein; Journal of Biological Chemistry; vol. 175; (1948); p. 575 View in Reaxys OH

OH OH

S OO

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Na2Cr2O7

2017-08-01 04:52:08

OH O

Rx-ID: 7067111 View in Reaxys 440/804 Yield

Conditions & References Produkt5:Azelainsaeure Kariyone; Fukui; Ishimasa; Yakugaku Zasshi; vol. 68; (1948); p. 272; ; (1951); p. 9479 View in Reaxys O–

Na + O

CO2 O

Rx-ID: 8426395 View in Reaxys 441/804 Yield

Conditions & References bei der Vergaerung durch Clostridium lactoacetophilum nov.spec. in Gegenwart von Acetat Bhat; Barker; ; vol. 56; (1948); p. 778; ; (1949); p. 2276 View in Reaxys

OH HO

Rx-ID: 198562 View in Reaxys 442/804 Yield

Conditions & References durch Clostridium acetobutylicum Simon; Archives of Biochemistry; vol. 14; (1947); p. 39 View in Reaxys

NH 2

Rx-ID: 200147 View in Reaxys 443/804 Yield

Conditions & References Anaerober Abbau durch Clostridium saccharobutyricum Cohen et al.; Bulletin de la Societe de Chimie Biologique; vol. 29; (1947); p. 646; Bulletin de la Societe de Chimie Biologique; vol. 30; (1948); p. 110 View in Reaxys

OH H HO

OH H

HO O

Rx-ID: 201099 View in Reaxys 444/804 Yield

Conditions & References Clostridium acetobutylicum bei der Vergaerung durch Simon; Archives of Biochemistry; vol. 14; (1947); p. 39 View in Reaxys

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O H HO

OH H

HO O

OH racemate

Rx-ID: 204512 View in Reaxys 445/804 Yield

Conditions & References durch Clostridium acetobutylicum; (Mechanismus der Bildung) Simon; Archives of Biochemistry; vol. 14; (1947); p. 39 View in Reaxys Janke; Siedler; Biochemische Zeitschrift; vol. 292; (1937); p. 111 View in Reaxys und aus anderen Kohlenhydraten durch Clostridium thermosaccharolyticum Sjolander; ; vol. 34; (1937); p. 419,424; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 1377 View in Reaxys durch Zymosarcina maxima Smit; ; vol. 36; (1933); p. 455; Chem. Zentralbl.; vol. 104; nb. II; (1933); p. 1377 View in Reaxys durch Schlammbakterien Tarvin; Buswell; Journal of the American Chemical Society; vol. 56; (1934); p. 1753 View in Reaxys bei der Vergaerung durch ein typisches Buttersaeure-Bacterium, das vermutlich zur Amylobacter-Gruppe gehoert Heiduschka; Reymann; ; vol. 70; (1929); p. 87; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 2196 View in Reaxys bei der Aceton-Butylalkohol-Gaerung durch Bac.granulobacter pectinovorum Speakman; Journal of Biological Chemistry; vol. 58; (1924); p. 398,400,404 View in Reaxys bei der Vergaerung durch Bac.granulobacter pectinovorum Speakman; Journal of Biological Chemistry; vol. 58; (1924); p. 398,400,404 View in Reaxys bei der Vergaerung durch Bakterien des Klaerschlammes Bach; Sierp; ; vol. <II>62; p. 51; Chem. Zentralbl.; vol. 95; nb. II; (1924); p. 1357 View in Reaxys Gaerung erfolgt mit Buttersaeurebacterien bei 35-40grad,Kreide hinzufuegen,nach 8-10 Tagen Calciumcarbonat abfiltrieren,Filtrat eindampfen,Calciumbutyrat mit Schwefelsaeure zersetzen,Buttersaeure destillieren und fraktionieren Szameitat; View in Reaxys durch Clostridium acetobutylicum; (Abhaengigkeit des Verlaufs von Reaktionsbedingungen) Langlykke; Peterson; Fred; ; vol. 34; (1937); p. 446; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 626 View in Reaxys Peldan; Suomen Kemistilehti A; vol. 11; (1938); p. 91; Suomen Kemistilehti B; vol. 11; (1938); p. 5; Chem. Zentralbl.; vol. 110; nb. II; (1939); p. 1684 View in Reaxys

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air

lead-oleate

manganese-oleate

cobalt-oleate

Rx-ID: 6188390 View in Reaxys 446/804 Yield

Conditions & References Patent; Polymer Prod.Ltd.; US2456549; (1947) View in Reaxys

concentrated NaOH

HO O

Rx-ID: 6188413 View in Reaxys 447/804 Yield

Conditions & References T= 240 °C , im Autoklaven Hargreaves; Owen; Journal of the Chemical Society; (1947); p. 750 View in Reaxys

O–

Na +

2-ethyl-hexanoic acid (1) O

Rx-ID: 6188417 View in Reaxys 448/804 Yield

Conditions & References T= 300 °C Weizmann; Sulzbacher; Bergmann; Journal of the Chemical Society; (1947); p. 851 View in Reaxys

concentrated KOH

HO O

Rx-ID: 7066089 View in Reaxys 449/804 Yield

Conditions & References T= 240 °C , im Autoklaven Hargreaves; Owen; Journal of the Chemical Society; (1947); p. 752 View in Reaxys

alkaline KMnO4 O

O OH

HO O

Rx-ID: 7066115 View in Reaxys 450/804 Yield

Conditions & References T= 50 - 70 °C Morton; Holden; Journal of the American Chemical Society; vol. 69; (1947); p. 1677,1679 View in Reaxys

187/263

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O O

Cl Al

O Si

O O

HO O

Rx-ID: 7066167 View in Reaxys 451/804 Yield

Conditions & References reagiert analog mit Toluol Petrow; Itkina; Zhurnal Obshchei Khimii; vol. 17; (1947); p. 220,222; ; (1948); p. 516 View in Reaxys OH

KO H

HO OH

Rx-ID: 7066688 View in Reaxys 452/804 Yield

Conditions & References T= 240 °C , Produkt5: Wasserstoff Hargreaves; Owen; Journal of the Chemical Society; (1947); p. 755 View in Reaxys

O–

Na +

heptane-carboxylic acid-(3)

OH O

Rx-ID: 7077067 View in Reaxys 453/804 Yield

Conditions & References T= 310 °C Weizmann; Sulzbacher; Bergmann; Journal of the Chemical Society; (1947); p. 851 View in Reaxys O

HO O

Rx-ID: 26202 View in Reaxys 454/804 Yield

Conditions & References Hydrogenation Patent; Eastman Kodak Co.; US2484498; (1946) View in Reaxys

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Rx-ID: 198259 View in Reaxys 455/804 Yield

Conditions & References bei der Ozonspaltung, (+-)-hept-2t-en-4-ol Young et al.; Journal of the American Chemical Society; vol. 68; (1946); p. 293,295 View in Reaxys

Raney nickel

Rx-ID: 5714600 View in Reaxys 456/804 Yield

Conditions & References T= 120 - 150 °C , p= 73550.8Torr , Hydrogenation Patent; Eastman Kodak Co.; US2484498; (1946) View in Reaxys

Raney nickel

Rx-ID: 5714601 View in Reaxys 457/804 Yield

Conditions & References T= 120 - 150 °C , p= 73550.8Torr , Hydrogenation Patent; Eastman Kodak Co.; US2484498; (1946) View in Reaxys

copper-zirconium

Rx-ID: 6684756 View in Reaxys 458/804 Yield

Conditions & References T= 250 - 350 °C Dolgow; Koton; Ssidorow; Zhurnal Obshchei Khimii; vol. 6; (1936); p. 1459; Chem. Zentralbl.; vol. 108; nb. I; (1937); p. 4086 View in Reaxys Koton; Barssukowa; Zhurnal Obshchei Khimii; vol. 16; (1946); p. 687; ; (1947); p. 1206 View in Reaxys

S HO

S OO

Rx-ID: 7066108 View in Reaxys 459/804 Yield

Conditions & References bei der Oxydation Smith; Rivett; ; vol. 31; p. 113,121; ; (1946); p. 6753 View in Reaxys

O O

HO O

Rx-ID: 6188431 View in Reaxys 460/804 Yield

Conditions & References With nickel carbonyl, steam, T= 314 - 324 °C , unter Druck

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Patent; du Pont de Nemours and Co.; US2448368; (1945) View in Reaxys

nickel phthalocyanin O O

O O

Rx-ID: 7066163 View in Reaxys 461/804 Yield

Conditions & References T= 120 °C Paquot; Bulletin de la Societe Chimique de France; vol. <5>12; (1945); p. 451 View in Reaxys

HO O

Rx-ID: 227625 View in Reaxys 462/804 Yield

Conditions & References bei der Ozonspaltung Powell; Hagemann; Journal of the American Chemical Society; vol. 66; (1944); p. 374 View in Reaxys

O OH

Rx-ID: 637282 View in Reaxys 463/804 Yield

Conditions & References With air, anhydrous cobalt diacetate Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425878; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2287803; (1938) View in Reaxys With air, acetate of Ce Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425878; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2287803; (1938) View in Reaxys With air, acetate of Hg Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys

190/263

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Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425878; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2287803; (1938) View in Reaxys With air, acetate of Pb Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425878; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2287803; (1938) View in Reaxys With air, acetate of Th Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425878; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2287803; (1938) View in Reaxys With air, acetate of V Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425878; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2287803; (1938) View in Reaxys With air, acetate of bi Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425878; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2287803; (1938) View in Reaxys

191/263

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HO O

Rx-ID: 791406 View in Reaxys 464/804 Yield

Conditions & References With air, mercury(II) diacetate, acetic acid, T= 30 - 50 °C , Reagens 4: Acetaldehyd Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys With air, acetic acid, bismuth triacetate, T= 30 - 50 °C , Reagens 4: Acetaldehyd Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys With vanadium (II) acetate, air, acetic acid, T= 30 - 50 °C , Reagens 4: Acetaldehyd Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys With air, Neutral lead acetate, acetic acid, T= 30 - 50 °C , Reagens 4: Acetaldehyd Patent; Eastman Kodak Co.; US2425882; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425880; (1944) View in Reaxys Patent; Eastman Kodak Co.; US2425881; (1944) View in Reaxys

cellulose

HO O

Rx-ID: 6188378 View in Reaxys 465/804 Yield

Conditions & References durch Darmbakterien Suomalainen; Arhimo; Biochemische Zeitschrift; vol. 317; (1944); p. 59 View in Reaxys durch Vergaerung und durch Vergaerung von cellulosehaltigen Abfaellen Loginowa; ; vol. 6; (1937); p. 1101; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 4544 View in Reaxys Perwoswanski; Tschelzowa; ; vol. 5; (1936); p. 385; Chem. Zentralbl.; vol. 108; nb. I; (1937); p. 3813 View in Reaxys Veldhuis; Christensen; Fulmer; Industrial and Engineering Chemistry; vol. 28; (1936); p. 431 View in Reaxys Acharya; Biochemical Journal; vol. 29; (1935); p. 528 View in Reaxys Tomoda; Yamaura; ; vol. 36; (1933); p. 436; Chem. Zentralbl.; vol. 105; nb. I; (1934); p. 559 View in Reaxys

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Raney nickel

Rx-ID: 7066068 View in Reaxys 466/804 Yield

Conditions & References T= 90 °C Schwenk et al.; Journal of Organic Chemistry; vol. 9; (1944); p. 175 View in Reaxys

chromic acid

Rx-ID: 7066079 View in Reaxys 467/804 Yield

Conditions & References Petjunin; ; (1944); p. 950 View in Reaxys

CuO

hydrogen

HO O

Rx-ID: 6188414 View in Reaxys 468/804 Yield

Conditions & References T= 100 - 250 °C , p= 57369.6Torr Takayasu; Nippon Kagaku Kaishi; vol. 64; (1943); p. 675,684; ; (1947); p. 3353 View in Reaxys

yeast

Rx-ID: 6684735 View in Reaxys 469/804 Yield

Conditions & References Lynen; Justus Liebigs Annalen der Chemie; vol. 554; (1943); p. 58 View in Reaxys

water containing Raney nickel

Rx-ID: 7066074 View in Reaxys 470/804 Yield

Conditions & References Mozingo et al.; Journal of the American Chemical Society; vol. 65; (1943); p. 1013,1015 View in Reaxys

water containing Raney nickel

Rx-ID: 7066075 View in Reaxys 471/804 Yield

Conditions & References Mozingo et al.; Journal of the American Chemical Society; vol. 65; (1943); p. 1013,1015 View in Reaxys

O O O

E O

OH HO

S OO

HO O

Rx-ID: 7066103 View in Reaxys 472/804

193/263

2017-08-01 04:52:08

Yield

Conditions & References T= -10 - -5 °C Montagne; Roch; Bulletin de la Societe Chimique de France; vol. <5> 10; (1943); p. 193,196 View in Reaxys

OH O

clostridium tetani

OH O O OH

OH O

Rx-ID: 7066137 View in Reaxys 473/804 Yield

Conditions & References Produkt5:CO2 Pickett; Journal of Biological Chemistry; vol. 151; (1943); p. 204 View in Reaxys

Rx-ID: 227230 View in Reaxys 474/804 Yield

Conditions & References With sulfuric acid Lippincott; Hass; Industrial and Engineering Chemistry; vol. 31; (1939); p. 119 View in Reaxys Patent; Purdue Res.Found.; US2113812; (1937) View in Reaxys With hydrogenchloride, propionic acid Patent; Comm.Solv.Corp.; US2381410; (1942) View in Reaxys With benzenesulfonic Acid Patent; Comm.Solv.Corp.; US2113813; (1937) View in Reaxys

O OH

air

metal acetate

Rx-ID: 6684759 View in Reaxys 475/804 Yield

Conditions & References T= 30 - 50 °C , unter Druck Patent; Eastman Kodak Co.; US2353159; (1942) View in Reaxys Patent; Eastman Kodak Co.; US2353157; (1942) View in Reaxys Patent; Eastman Kodak Co.; US2353158; (1942) View in Reaxys T= 150 °C , unter Druck Patent; Eastman Kodak Co.; US2353159; (1942) View in Reaxys Patent; Eastman Kodak Co.; US2353157; (1942) View in Reaxys

194/263

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Patent; Eastman Kodak Co.; US2353158; (1942) View in Reaxys

N O

H 2N

Rx-ID: 7066113 View in Reaxys 476/804 Yield

Conditions & References T= 140 - 158 °C Patent; Comm.Solv.Corp.; US2381410; (1942) View in Reaxys

air

aldehyde

cobalt salt

hexanol-(2)-acetate O

Rx-ID: 7077315 View in Reaxys 477/804 Yield

Conditions & References Patent; Eastman Kodak Co.; US2354683; (1942) View in Reaxys

O OH

Rx-ID: 242451 View in Reaxys 478/804 Yield

Conditions & References Hydrolysis Whitmore et al.; Journal of the American Chemical Society; vol. 63; (1941); p. 647 View in Reaxys

hydrogen

Raney nickel

Rx-ID: 7449260 View in Reaxys 479/804 Yield

Conditions & References T= 250 °C , p= 73550.8 - 147102Torr McClellan; Connor; Journal of the American Chemical Society; vol. 63; (1941); p. 484,486 View in Reaxys

sulfuric acid (5-7 percent )

MnSO4

lead anodes

HO O

Rx-ID: 6684734 View in Reaxys 480/804 Yield

Conditions & References Ausbeute z.B. 60prozent

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Jerschow; Pjatnitzkaja; ; nb. 1; (1940); p. 29; ; (1940); p. 4673 View in Reaxys

H2SO4 (10-15 percent )

lead anode

Ce(SO4)2

O O

Rx-ID: 6684758 View in Reaxys 481/804 Yield

Conditions & References Produkt5:CO2 Radtschenko; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 13; (1940); p. 1348; ; (1941); p. 2469 View in Reaxys

KMnO4 O

diluted natrium carbonate

HO O

Rx-ID: 7066129 View in Reaxys 482/804 Yield

Conditions & References Karassew; Chabarowa; Zhurnal Obshchei Khimii; vol. 10; (1940); p. 1645; Chem. Zentralbl.; vol. 113; nb. I; (1942); p. 28 View in Reaxys

Z O O

OH O

Rx-ID: 206624 View in Reaxys 483/804 Yield

Conditions & References T= 320 - 325 °C , und andere Produkten: Wasser,CO2,Kohlenwasserstoff,Propionsaeure Brambilla; ; vol. 29; (1939); p. 303; Chem. Zentralbl.; vol. 110; nb. II; (1939); p. 4394 View in Reaxys O

OH O

Rx-ID: 645851 View in Reaxys 484/804 Yield

Conditions & References durch Aerobacter indologenes Mickelson,Werkman; ; vol. 37; (1939); p. 623; Chem. Zentralbl.; vol. 110; nb. II; (1939); p. 2342 View in Reaxys

copper uranium

hydrogen

196/263

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HO OH O

Rx-ID: 6208007 View in Reaxys 485/804 Yield

Conditions & References T= 255 - 275 °C Abramowa; Dolgow; Zhurnal Obshchei Khimii; vol. 9; (1939); p. 1979; Chem. Zentralbl.; vol. 111; nb. I; (1940); p. 2455 View in Reaxys

acetic acid and propionic acid O

Rx-ID: 6209284 View in Reaxys 486/804 Yield

Conditions & References With nitric acid, T= 90 - 95 °C Patent; Sharples Chem.Inc.; US2267377; (1939) View in Reaxys

N HO

H 2N

S OO

HO O

Rx-ID: 7066112 View in Reaxys 487/804 Yield

Conditions & References T= 140 - 158 °C Lippincott; Hass; Industrial and Engineering Chemistry; vol. 31; (1939); p. 119 View in Reaxys Patent; Purdue Res.Found.; US2113812; (1938) View in Reaxys

KMnO4

O O HO

OH O

Rx-ID: 7066117 View in Reaxys 488/804 Yield

Conditions & References Kass; Burr; Journal of the American Chemical Society; vol. 61; (1939); p. 3293 View in Reaxys

+ Br– Mg

CO2

HO OH

HO O

Rx-ID: 8264138 View in Reaxys 489/804 Yield

Conditions & References Produkt 5: Hexan Tuot; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 208; (1939); p. 1026 View in Reaxys Mousseron; Granger; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 988; Bulletin de la Societe Chimique de France; (1946); p. 253 View in Reaxys

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O HO O

Rx-ID: 157059 View in Reaxys 490/804 Yield

Conditions & References T= 20 °C Wojack; Chemische Berichte; vol. 71; (1938); p. 1102,1114 View in Reaxys

OH O

NH 2

Rx-ID: 203286 View in Reaxys 491/804 Yield

Conditions & References bei der Einw. von Clostridium tetanomorphum Woods; Clifton; Biochemical Journal; vol. 32; (1938); p. 345,349 View in Reaxys

HO O

Rx-ID: 648846 View in Reaxys 492/804 Yield

Conditions & References bei der Einw. von Clostridium tetanomorphum Woods; Clifton; Biochemical Journal; vol. 32; (1938); p. 345,349 View in Reaxys

C4H9TeOOH+2(C4H9)2TeO

H O

Rx-ID: 7070674 View in Reaxys 493/804 Yield

Conditions & References Balfe; Chaplin; Phillips; Journal of the Chemical Society; (1938); p. 345 View in Reaxys

C O

HO O

Rx-ID: 6188382 View in Reaxys 494/804 Yield

Conditions & References With hydrogen, im Gegenwart von Katalysatoren Koch; Pichler; Koelbel; Brennstoff-Chemie; vol. 16; (1935); p. 382; Chem. Zentralbl.; vol. 106; nb. II; (1935); p. 4009 View in Reaxys Natta; ; vol. 40; (1937); p. 162; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 286 View in Reaxys With hydrogen, im Gegenwart von Katalysatoren Strada; ; vol. 16; (1934); p. 62; Chem. Zentralbl.; vol. 105; nb. II; (1934); p. 1530 View in Reaxys

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Raney nickel

OH O

Rx-ID: 6208006 View in Reaxys 495/804 Yield

Conditions & References Delepine; Hanegraaff; Bulletin de la Societe Chimique de France; vol. <5> 4; (1937); p. 2087,2091 View in Reaxys Delepine; Horeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 1607; Bulletin de la Societe Chimique de France; vol. <5>4; (1937); p. 1531 View in Reaxys

methane and acetic acid and caproic acid O

Rx-ID: 6215750 View in Reaxys 496/804 Yield

Conditions & References Vergaerung durch eine Mischkultur von Methanobacterium omelianskii und einer Plectridiumart in CO2-Atmosphaere Barker; ; vol. 8; (1937); p. 415; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 2638 View in Reaxys

H2SO4 (10-15 percent )

lead anode

Ce(SO4)2

HO O

Rx-ID: 6684742 View in Reaxys 497/804 Yield

Conditions & References Radtschenko; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 10; (1937); p. 683; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 13; (1940); p. 1348; ; (1941); p. 2469; Chem. Zentralbl.; vol. 109; nb. I; (1938); p. 294 View in Reaxys

KMnO4

Rx-ID: 7066055 View in Reaxys 498/804 Yield

Conditions & References Lemke; Tischtschenko; Zhurnal Obshchei Khimii; vol. 7; (1937); p. 1995,1998; Chem. Zentralbl.; vol. 110; nb. I; (1939); p. 2398 View in Reaxys

permanganate

HO O

Rx-ID: 7066065 View in Reaxys 499/804 Yield

Conditions & References Delaby; Lecomte; Bulletin de la Societe Chimique de France; vol. <5> 4; (1937); p. 1007,1011 View in Reaxys

E O

Raney nickel

diluted NaOH

HO O

OH OH

Rx-ID: 7066069 View in Reaxys 500/804

199/263

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Yield

Conditions & References Delepine; Horeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 1607; Bulletin de la Societe Chimique de France; vol. <5>4; (1937); p. 1531 View in Reaxys

O O

H 2N

Rx-ID: 7066114 View in Reaxys 501/804 Yield

Conditions & References T= 140 - 158 °C Patent; Comm.Solv.Corp.; US2113813; (1937) View in Reaxys

sodium

OH O

Rx-ID: 7066686 View in Reaxys 502/804 Yield

Conditions & References Oskerko; ; vol. 4; (1937); p. 199; Chem. Zentralbl.; vol. 109; nb. II; (1938); p. 2586 View in Reaxys

Rx-ID: 17627 View in Reaxys 503/804 Yield

Conditions & References T= 470 °C Bilger; Hibbert; Journal of the American Chemical Society; vol. 58; (1936); p. 825 View in Reaxys

HO OH

Rx-ID: 101721 View in Reaxys 504/804 Yield

Conditions & References bei der Einw. von Clostridium butyricum in Kornschrotmaische; Produkt5: Aceton Bernhauer et al.; Biochemische Zeitschrift; vol. 287; (1936); p. 62 View in Reaxys

HO O

Rx-ID: 650990 View in Reaxys 505/804 Yield

Conditions & References T= 470 - 478 °C Bilger; Hibbert; Journal of the American Chemical Society; vol. 58; (1936); p. 825 View in Reaxys

methanobacterium Omelianskii

HO O

Rx-ID: 6684738 View in Reaxys 506/804

200/263

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Yield

Conditions & References Barker; Journal of Biological Chemistry; vol. 7; (1936); p. 157,411,437; Chem. Zentralbl.; vol. 108; nb. I; (1937); p. 1707 View in Reaxys

copper cerium

O O

Rx-ID: 6684755 View in Reaxys 507/804 Yield

Conditions & References T= 250 - 350 °C Dolgow; Koton; Leltschuk; ; vol. 1; (1936); p. 73; Chem. Zentralbl.; vol. 107; nb. II; (1936); p. 1061 View in Reaxys

CaCO3

HO OH O

Rx-ID: 6711835 View in Reaxys 508/804 Yield

Conditions & References bei der Einw. von Clostridium butyricum in Kornschrotmaische; Produkt5: Aceton Bernhauer et al.; Biochemische Zeitschrift; vol. 287; (1936); p. 62 View in Reaxys

NaOH (1-2 n)

iron electrodes

olefins O

Rx-ID: 6730220 View in Reaxys 509/804 Yield

Conditions & References Kurenniemi; Tommila; Suomen Kemistilehti B; vol. 9; (1936); p. 25; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 205 View in Reaxys

NaOH (1-2 n)

nickel electrodes

olefins O

Rx-ID: 6730221 View in Reaxys 510/804 Yield

Conditions & References Kurenniemi; Tommila; Suomen Kemistilehti B; vol. 9; (1936); p. 25; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 205 View in Reaxys

NaOH (1-2 n)

OH H

platinum electrodes

olefins

saturated hydrocarbon

Rx-ID: 6731214 View in Reaxys 511/804 Yield

Conditions & References bei der elektrochemischen Oxydation

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Kurenniemi; Tommila; Suomen Kemistilehti B; vol. 9; (1936); p. 25; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 205 View in Reaxys

calcium hypochlorite

HO O

Rx-ID: 7066150 View in Reaxys 512/804 Yield

Conditions & References Ssuknewitsch; Tschilingarjan; Chemische Berichte; vol. 69; (1936); p. 1542 View in Reaxys

Ca(OCl)2

HO O

Rx-ID: 7066151 View in Reaxys 513/804 Yield

Conditions & References Ssuknewitsch; Tschilingarjan; Chemische Berichte; vol. 69; (1936); p. 1542 View in Reaxys

nickel

OH H

HO O

Rx-ID: 7066154 View in Reaxys 514/804 Yield

Conditions & References elektrolytische Oxydation; Produkt5: CO2 Tommila; Annales Academiae Scientiarum Fennicae, Series A; vol. 46; nb. 6; (1936); p. 83; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 204 View in Reaxys

Ca(OCl)2

Rx-ID: 7067109 View in Reaxys 515/804 Yield

Conditions & References Ssuknewitsch; Tschilingarjan; Chemische Berichte; vol. 69; (1936); p. 1542 View in Reaxys

HO OH

Rx-ID: 197435 View in Reaxys 516/804 Yield

Conditions & References Clostridium butyricum Bernhauer; Kueerschner; Biochemische Zeitschrift; vol. 280; (1935); p. 381 View in Reaxys

HO O

Rx-ID: 718241 View in Reaxys 517/804 Yield

Conditions & References Destillieren Werntz; Journal of the American Chemical Society; vol. 57; (1935); p. 205 View in Reaxys

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diluted HNO3

Rx-ID: 7066116 View in Reaxys 518/804 Yield

Conditions & References T= 90 °C Wiljams; Smirnow; Golmow; Zhurnal Obshchei Khimii; vol. 5; (1935); p. 1197; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 3347 View in Reaxys

Rx-ID: 7066119 View in Reaxys 519/804 Yield

Conditions & References Bockemueller; Hoffmann; Justus Liebigs Annalen der Chemie; vol. 519; (1935); p. 165,191 View in Reaxys

KMnO4

Rx-ID: 7067112 View in Reaxys 520/804 Yield

Conditions & References T= 25 °C Wiljams; Smirnow; Golmow; Zhurnal Obshchei Khimii; vol. 5; (1935); p. 1197; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 3347 View in Reaxys

succinaldehydic acid

O O

Rx-ID: 7087121 View in Reaxys 521/804 Yield

Conditions & References der Amylester reagiert bei der Ozonspaltung; Produkt 5:Bernsteinsaeure; P.6:Bernsteinsaeuremonoamylester; P. 7:Bernsteinaldehydsaeureamylester

Toyama; Tsuchiya; Bulletin of the Chemical Society of Japan; vol. 10; (1935); p. 297 View in Reaxys O O

ZnCl2

HO O

Rx-ID: 7449257 View in Reaxys 522/804 Yield

Conditions & References Underwood; Baril; Journal of the American Chemical Society; vol. 57; (1935); p. 2729 View in Reaxys

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OH OH HO

K2cr2O7

S OO

racemate

trans(?)-tetrahydroionone O

Rx-ID: 8289423 View in Reaxys 523/804 Yield

Conditions & References Salkind; Soniss; Blochin; Doklady Akademii Nauk SSSR; (1935); p. II 57, 58, 61; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 4169 View in Reaxys

Rx-ID: 101720 View in Reaxys 524/804 Yield

Conditions & References bei der Einw. von Rhizobium trifolii auf Calciumlactat Virtanen; Nordlund; Hollo; Biochemical Journal; vol. 28; (1934); p. 799 View in Reaxys

O– Na +

O O

Rx-ID: 333136 View in Reaxys 525/804 Yield

Conditions & References folgendes Verseifen Rodriguez Velasco; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 32; (1934); p. 809; Chem. Zentralbl.; vol. 106; nb. I; (1935); p. 2805 View in Reaxys N

E O

Rx-ID: 7066049 View in Reaxys 526/804 Yield

Conditions & References Rambaud; Bulletin de la Societe Chimique de France; vol. <5> 1; (1934); p. 1317,1335; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 220; (1945); p. 742 View in Reaxys O E

(v4)

HO O

Rx-ID: 7066122 View in Reaxys 527/804 Yield

Conditions & References Fraser; Kon; Journal of the Chemical Society; (1934); p. 608 View in Reaxys

syrupy phosphoric acid

HO O

Rx-ID: 7920377 View in Reaxys 528/804

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Yield

Conditions & References Sprague; Adkins; Journal of the American Chemical Society; vol. 56; (1934); p. 2669,2671 View in Reaxys

O HO

HO O

HO racemate

Rx-ID: 203995 View in Reaxys 529/804 Yield

Conditions & References durch Zymosarcina maxima Smit; ; vol. 36; (1933); p. 455; Chem. Zentralbl.; vol. 104; nb. II; (1933); p. 1377 View in Reaxys

O O

potassium permanganate

Br racemate

Br O HO

O HO

Rx-ID: 5714603 View in Reaxys 530/804 Yield

Conditions & References Erdtman; Justus Liebigs Annalen der Chemie; vol. 503; (1933); p. 283,289 View in Reaxys

C O

HO O

Rx-ID: 6188432 View in Reaxys 531/804 Yield

Conditions & References With boron trifluoride, T= 200 - 400 °C , unter Druck Patent; du Pont; US2162459; (1933) View in Reaxys

HO OH

O O

Rx-ID: 6684750 View in Reaxys 532/804 Yield

Conditions & References einfluss verschiedener Katalysatoren Rubinstein et al.; Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation); vol. 6; (1933); p. 278; Chem. Zentralbl.; vol. 105; nb. I; (1934); p. 1709 View in Reaxys

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air

O O

Rx-ID: 6684751 View in Reaxys 533/804 Yield

KMnO4

HO O

Rx-ID: 7066086 View in Reaxys 534/804 Yield

Conditions & References Landa; Cech; Sliva; Collection of Czechoslovak Chemical Communications; vol. 5; (1933); p. 208 View in Reaxys

oxygen

OH O

HO O

ketone C9H18O O

Rx-ID: 7079349 View in Reaxys 535/804 Yield

Conditions & References T= 115 °C Dupont; Chavanne; Bulletin des Societes Chimiques Belges; vol. 42; (1933); p. 537 View in Reaxys O

(v4)

OH O

Rx-ID: 8264141 View in Reaxys 536/804 Yield

Conditions & References anschliessendes Behandeln mit wss. H2O2 Blomquist; Marvel; Journal of the American Chemical Society; vol. 55; (1933); p. 1655,1662 View in Reaxys

4-oxo-1-ethyl-2.2.5-tripropyl-cyclopentene-(5)

OH O

Rx-ID: 8264142 View in Reaxys 537/804 Yield

Conditions & References With tetrachloromethane, ozone, anschliessendes Behandeln mit wss. H2O2

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Blomquist; Marvel; Journal of the American Chemical Society; vol. 55; (1933); p. 1655,1662 View in Reaxys

H HO

O O

Rx-ID: 440553 View in Reaxys 538/804 Yield

Conditions & References Aufbewahren Rona; Chain; Ammon; Biochemische Zeitschrift; vol. 247; (1932); p. 113,119 View in Reaxys

O O

Rx-ID: 476502 View in Reaxys 539/804 Yield

Conditions & References Rona; Chain; Ammon; Biochemische Zeitschrift; vol. 247; (1932); p. 113,119 View in Reaxys O

Rx-ID: 6188416 View in Reaxys 540/804 Yield

Conditions & References T= 110 - 112 °C Marshall; Recueil des Travaux Chimiques des Pays-Bas; vol. 51; (1932); p. 234 View in Reaxys Norris; Young; Journal of the American Chemical Society; vol. 52; (1930); p. 5069 View in Reaxys

bacterium aceti

Rx-ID: 6684731 View in Reaxys 541/804 Yield

Conditions & References Mosel; ; vol. 87 II; (1932); p. 211; Chem. Zentralbl.; vol. 104; nb. I; (1933); p. 1306 View in Reaxys

bacterium ascendens

Rx-ID: 6684732 View in Reaxys 542/804 Yield

Conditions & References Mosel; ; vol. 87 II; (1932); p. 211; Chem. Zentralbl.; vol. 104; nb. I; (1933); p. 1306 View in Reaxys

Cl OH

Ca(OCl)2

Rx-ID: 6684760 View in Reaxys 543/804

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Yield

Conditions & References Sssuknewitsch; Tschilingarjan; Zhurnal Obshchei Khimii; vol. 2; (1932); p. 789; Chemische Berichte; vol. 68; (1935); p. 1216; Chem. Zentralbl.; vol. 104; nb. II; (1933); p. 1171 View in Reaxys

aqueous KMnO4

Rx-ID: 7066053 View in Reaxys 544/804 Yield

Conditions & References Kuhn; Hoffer; Chemische Berichte; vol. 65; (1932); p. 172,174 View in Reaxys

OH HO

Cr2O3-H2SO4

Rx-ID: 7066054 View in Reaxys 545/804 Yield

Conditions & References solid form Bloomfield; Farmer; Journal of the Chemical Society; (1932); p. 2064,2068 View in Reaxys

O O

sodium amalgam OH

Rx-ID: 7066072 View in Reaxys 546/804 Yield

Conditions & References Hydrolyse mit alkoh.KOH und Oxydation mit alkal.Chromschwefelsaeure-Loesung Bloomfield; Farmer; Journal of the Chemical Society; (1932); p. 2064,2068 View in Reaxys

KMnO4

O O

OH O

Rx-ID: 7066100 View in Reaxys 547/804 Yield

Conditions & References Produkt 5:Malonsaeure; P.6:Oxalsaeure Inoue; Sahashi; Proceedings of the Imperial Academy (Tokyo); vol. 8; (1932); p. 371; Chem. Zentralbl.; vol. 104; nb. I; (1933); p. 1427 View in Reaxys

O O

sodium amalgam OH

O O

Rx-ID: 7066143 View in Reaxys 548/804 Yield

Conditions & References Hydrolyse mit alkoh.KOH und Oxydation mit alkal.KMnO4-Loesung Bloomfield; Farmer; Journal of the Chemical Society; (1932); p. 2064,2068 View in Reaxys

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O H

potassium permanganate

Rx-ID: 7066149 View in Reaxys 549/804 Yield

Conditions & References Witzemann; Journal of Biological Chemistry; vol. 95; (1932); p. 235,258 View in Reaxys

Cr2O3-H2SO4

HO Cl

OH O

Rx-ID: 7066170 View in Reaxys 550/804 Yield

Conditions & References liquid form Bloomfield; Farmer; Journal of the Chemical Society; (1932); p. 2064,2068 View in Reaxys

1-phenyl-butene-(1) O

Rx-ID: 8264139 View in Reaxys 551/804 Yield

Conditions & References Erhitzen Rona; Chain; Ammon; Biochemische Zeitschrift; vol. 247; (1932); p. 113,119 View in Reaxys

OH H

HO O

Rx-ID: 99544 View in Reaxys 552/804 Yield

Conditions & References With carbon, CaI2, T= 200 - 375 °C , unter Druck Patent; du Pont de Nemours and Co.; US2013338; (1931) View in Reaxys

O– Na +

Rx-ID: 847177 View in Reaxys 553/804 Yield

Conditions & References Snell; McElvain; Journal of the American Chemical Society; vol. 53; (1931); p. 752,754; ; vol. Vol.II; (1943); p. 115 View in Reaxys

(v4)

oxygen

Rx-ID: 6188411 View in Reaxys 554/804 Yield

Conditions & References Fischer; Duell; Volz; Justus Liebigs Annalen der Chemie; vol. 486; (1931); p. 87,90,92,93 View in Reaxys

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Z Cl

palladium-barium sulfate

HO O

Rx-ID: 7066077 View in Reaxys 555/804 Yield

Conditions & References Geschwindigkeit.Hydrogenation Paal; Schiedewitz; Rauscher; Chemische Berichte; vol. 64; (1931); p. 1523,1525,1529 View in Reaxys

palladium-barium sulfate

Z O

HO O

Rx-ID: 7066090 View in Reaxys 556/804 Yield

Conditions & References Geschwindigkeit.Hydrogenation Paal; Schiedewitz; Rauscher; Chemische Berichte; vol. 64; (1931); p. 1523,1525,1529 View in Reaxys

dibutyryl

HO O

Rx-ID: 7066102 View in Reaxys 557/804 Yield

Conditions & References With sodium ethanolate, benzene Snell; McElvain; Journal of the American Chemical Society; vol. 53; (1931); p. 752,754; ; vol. Vol.II; (1943); p. 115 View in Reaxys

palladium-barium sulfate

Rx-ID: 7066059 View in Reaxys 558/804 Yield

Conditions & References Geschwindigkeit.Hydrogenation Paal; Schiedewitz; Chemische Berichte; vol. 63; (1930); p. 768 View in Reaxys

air O

Z O

OH H

O O

Rx-ID: 7066095 View in Reaxys 559/804 Yield

Conditions & References beim Stehenlassen unter Lichtzutritt Taeufel; Mueller; Biochemische Zeitschrift; vol. 219; (1930); p. 342,348 View in Reaxys

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ZnCl2

Rx-ID: 7066121 View in Reaxys 560/804 Yield

Conditions & References entstehen auch Polymerisationsprodukten vom Isopropylaethylen Underwood; Baril; Journal of the American Chemical Society; vol. 52; (1930); p. 395,396; Journal of the American Chemical Society; vol. 53; (1931); p. 2200,2202 View in Reaxys

KMnO4

natrium carbonate

HO O

Rx-ID: 7066130 View in Reaxys 561/804 Yield

Conditions & References Eccott; Linstead; Journal of the Chemical Society; (1930); p. 911 View in Reaxys

OH O

HO O

Rx-ID: 102681 View in Reaxys 562/804 Yield

Conditions & References T= 301 - 304 °C Vogel; Journal of the Chemical Society; (1929); p. 732 View in Reaxys T= 300 - 304 °C Vogel; Journal of the Chemical Society; (1929); p. 732 View in Reaxys

HO O

Rx-ID: 180159 View in Reaxys 563/804 Yield

Conditions & References With ozone, T= -15 °C Weygand; Baumgaertel; Chemische Berichte; vol. 62; (1929); p. 578 View in Reaxys

calcium salt of/the/ α-chloro-butyric acid

HO O

Rx-ID: 6188369 View in Reaxys 564/804 Yield

Conditions & References With ethanol, palladium, Hydrogenation Paal; Schiedewitz; Chemische Berichte; vol. 62; (1929); p. 1937,1938 View in Reaxys

corn

HO O

Rx-ID: 6188381 View in Reaxys 565/804 Yield

Conditions & References bei der Vergaerung durch Clostridium acetobutylicum

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Stiles; Peterson; Fred; Journal of Biological Chemistry; vol. 84; (1929); p. 444 View in Reaxys bei der Vergaerung durch einen Erreger der Aceton-Butylalkohol-Gaerung Reilly et al.; Biochemical Journal; vol. 14; (1920); p. 233,237 View in Reaxys

(v4)

N H

H N

HO O

Rx-ID: 6684762 View in Reaxys 566/804 Yield

Conditions & References T= -15 °C , aufeinanderfolgende Behandlung des Reaktionsgemisches mit Wasser und Phenylhydrazin Weygand; Baumgaertel; Chemische Berichte; vol. 62; (1929); p. 578 View in Reaxys

hydrogen

palladium

barium sulfate

HO O

Rx-ID: 7066061 View in Reaxys 567/804 Yield

Conditions & References das Calciumsalz reagiert Paal; Schiedewitz; Chemische Berichte; vol. 62; (1929); p. 1937,1938 View in Reaxys Paal; Schiedewitz; Chemische Berichte; vol. 62; (1929); p. 1937,1938 View in Reaxys O OH

hydrogen

palladium

barium sulfate

HO O

Rx-ID: 7066062 View in Reaxys 568/804 Yield

Conditions & References Paal; Schiedewitz; Chemische Berichte; vol. 62; (1929); p. 1937,1938 View in Reaxys das Calciumsalz reagiert Paal; Schiedewitz; Chemische Berichte; vol. 62; (1929); p. 1937,1938 View in Reaxys

permanganate

HO O

Rx-ID: 7066064 View in Reaxys 569/804 Yield

Conditions & References Koelsch; McElvain; Journal of the American Chemical Society; vol. 51; (1929); p. 3393 View in Reaxys

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HO O

Rx-ID: 247830 View in Reaxys 570/804 Yield

Conditions & References With oxygen, T= 300 °C Landa; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 187; (1928); p. 948 View in Reaxys

α-oxy-butyrate sodium

Rx-ID: 6188361 View in Reaxys 571/804 Yield

Conditions & References With nickel oxide, water, hydrogen, T= 245 - 250 °C , p= 42560Torr , Reagens 4:Aluminiumoxyd Rasuwajew; Chemische Berichte; vol. 61; (1928); p. 638; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 60; (1928); p. 914 View in Reaxys

oxime of propyl-n-pentyl ketone

H 2N

Rx-ID: 6188424 View in Reaxys 572/804 Yield

Conditions & References With hydrogenchloride, sulfuric acid Karrer et al.; Helvetica Chimica Acta; vol. 11; (1928); p. 1083; Helvetica Chimica Acta; vol. 15; (1932); p. 234 View in Reaxys With sulfuric acid, und Kochen des entstandenen Saeureamids mit konz.Salzsaeure Karrer et al.; Helvetica Chimica Acta; vol. 11; (1928); p. 1083; Helvetica Chimica Acta; vol. 15; (1932); p. 234 View in Reaxys O

hydrogen

nickel oxide

aluminium oxide

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high-melting α-methyl-α'-ethyl-succinic acid O

Rx-ID: 6214357 View in Reaxys 573/804 Yield

Conditions & References T= 280 - 290 °C , p= 53200Torr , beim Behandeln des Natriumsalzes Ipatjew; Rasuwajew; Chemische Berichte; vol. 61; (1928); p. 636; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 60; (1928); p. 911 View in Reaxys

copper

O O

Rx-ID: 6684753 View in Reaxys 574/804 Yield

Conditions & References T= 300 °C Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys Nomura; el Choi; Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron.; vol. 17; p. 708; Chem. Zentralbl.; vol. 99; nb. II; (1928); p. 1325 View in Reaxys

OH HO

(v1)

Na + -1

S OO

vanadium pentoxide

Cl OO

O O

Rx-ID: 6684757 View in Reaxys 575/804 Yield

Conditions & References Milas; Journal of the American Chemical Society; vol. 50; (1928); p. 496 View in Reaxys

S OO

H 2N

Rx-ID: 7066120 View in Reaxys 576/804 Yield

Conditions & References und beim Kochen des entstandenen Saeureamids mit konz.Salzsaeure Karrer et al.; Helvetica Chimica Acta; vol. 11; (1928); p. 1083; Helvetica Chimica Acta; vol. 15; (1932); p. 234 View in Reaxys

permanganate

Rx-ID: 7066148 View in Reaxys 577/804 Yield

Conditions & References Prevost; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 187; (1928); p. 946 View in Reaxys OH

chromic acid

potassium disulfate

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HO O

Rx-ID: 7066175 View in Reaxys 578/804 Yield

Conditions & References Venus-Danilowa; Bulletin de la Societe Chimique de France; vol. <4>43; (1928); p. 581 View in Reaxys Faworski; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 60; (1928); p. 410 View in Reaxys O–

HO 2

Ca 2+ O

Rx-ID: 628765 View in Reaxys 579/804 Yield

Conditions & References bei der Vergaerung durch eine Mischkultur von zwei nicht bezeichneten Bakterien Schaposchnikow; Sacharow; ; nb. 18; (1927); p. 13,25; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 1713 View in Reaxys O–

HO 2

Ca 2+

O 5 H

Rx-ID: 737775 View in Reaxys 580/804 Yield

Conditions & References bei der Vergaerung mit einer Mischkultur von zwei nicht naeher bezeichneten Bakterien; Produkt 5: Capronsaeure Schaposchnikow; Sacharow; ; nb. 18; (1927); p. 13,23,25; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 1713 View in Reaxys N OH HO

S OO

permanganate

HO O

Rx-ID: 5714604 View in Reaxys 581/804 Yield

Conditions & References T= 70 °C Delepine; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 184; (1927); p. 207; Bulletin de la Societe Chimique de France; vol. <4> 41; (1927); p. 392 View in Reaxys

α-oxy-α-methyl-α'-ethyl-succinate sodium

HO O

Rx-ID: 6188360 View in Reaxys 582/804 Yield

Conditions & References With nickel oxide, water, hydrogen, T= 245 - 250 °C , p= 45600Torr , Reagens 4:Aluminiumoxyd Rasuwajew; Chemische Berichte; vol. 60; (1927); p. 1979; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 1075 View in Reaxys

air

silver-asbestos

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HO O

H 2N 2

carbon monoxide O

Rx-ID: 6726936 View in Reaxys 583/804 Yield

Conditions & References T= 310 - 330 °C Ottensooser; Bulletin de la Societe Chimique de France; vol. <4> 41; (1927); p. 324 View in Reaxys

OH OH

hydrogen

nickel oxide

aluminium oxide

OH O

Rx-ID: 7066135 View in Reaxys 584/804 Yield

Conditions & References T= 245 - 250 °C , p= 45600Torr , Reaktion des Natriumsalzes Rasuwajew; Chemische Berichte; vol. 60; (1927); p. 1979; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 1075 View in Reaxys

chromic acid

Rx-ID: 7066171 View in Reaxys 585/804 Yield

Conditions & References Suida; Poell; Monatshefte fuer Chemie; vol. 48; (1927); p. 169,179; Angewandte Chemie; vol. 40; (1927); p. 506 View in Reaxys

permanganate solution

OH O

γ-butyryl-butyric acid

OH O

Rx-ID: 7449258 View in Reaxys 586/804 Yield

Conditions & References T= 0 °C Chavanne; Becker; Bulletin des Societes Chimiques Belges; vol. 36; (1927); p. 594; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 1169 View in Reaxys O

N O

HO O

O HO

Rx-ID: 412967 View in Reaxys 587/804 Yield

Conditions & References δ.δ-bis-<4-oxy-phenyl>-δ-valerolactone

216/263

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Dutt; Journal of the Chemical Society; (1926); p. 1135 View in Reaxys

HO O

Rx-ID: 420439 View in Reaxys 588/804 Yield

Conditions & References beim Aufbewahren, dextrorotatory substance Rupe; Perret; Helvetica Chimica Acta; vol. 9; (1926); p. 107 View in Reaxys

–O

Cr 3+

Rx-ID: 846243 View in Reaxys 589/804 Yield

Conditions & References van Risseghem; Bulletin des Societes Chimiques Belges; vol. 35; (1926); p. 332,342; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 53 View in Reaxys

permanganate

HO O

Rx-ID: 7066063 View in Reaxys 590/804 Yield

Conditions & References Dumoulin; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 975 View in Reaxys

α.α'-diethyl-acetone-α.α'-dicarboxylic acid O

Rx-ID: 7066082 View in Reaxys 591/804 Yield

Conditions & References With barium dihydroxide Schroeter; Chemische Berichte; vol. 59; (1926); p. 990; Chemische Berichte; vol. 49; (1916); p. 2716 View in Reaxys

aq. barium hydroxide solution

OH O

Rx-ID: 7066083 View in Reaxys 592/804 Yield

Conditions & References Schroeter; Chemische Berichte; vol. 59; (1926); p. 990; Chemische Berichte; vol. 49; (1916); p. 2716 View in Reaxys

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permanganate

Rx-ID: 7067110 View in Reaxys 593/804 Yield

Conditions & References Kirrmann; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 1630; Bulletin de la Societe Chimique de France; vol. <4> 41; (1927); p. 319,321 View in Reaxys O–

Na +

water

hydrogen

nickel (II)-oxide

methylethylacetic acid (?) O

Rx-ID: 8427139 View in Reaxys 594/804 Yield

Conditions & References T= 270 °C , p= 53200Torr , in Gegenwart Tonerde; Produkt 5: dl-Brenzweinsaeure Ipatjew; Rasuwajew; Chemische Berichte; vol. 59; (1926); p. 2032; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 58; (1926); p. 1347 View in Reaxys

+ Br– Mg

H 2N 2

Rx-ID: 172006 View in Reaxys 595/804 Yield

Conditions & References T= -20 °C Iwanow; Bulletin de la Societe Chimique de France; vol. <4>37; (1925); p. 289,293; Bulletin de la Societe Chimique de France; vol. <4>43; (1928); p. 443 View in Reaxys

O O

OH O

Rx-ID: 247406 View in Reaxys 596/804 Yield

Conditions & References bei der Kalischmelze Kon; Smith; Thorpe; Journal of the Chemical Society; vol. 127; (1925); p. 570 View in Reaxys

O O

HO O

OH O

H 2N 2

Rx-ID: 249565 View in Reaxys 597/804 Yield

Conditions & References T= 180 °C , bei der Zersetzung Brunner; Helvetica Chimica Acta; vol. 8; (1925); p. 653 View in Reaxys

OH O

H 2N 2

HO O

Rx-ID: 533531 View in Reaxys 598/804

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Yield

Conditions & References With diethyl ether Iwanow; Bulletin de la Societe Chimique de France; vol. <4>37; (1925); p. 289,293; Bulletin de la Societe Chimique de France; vol. <4>43; (1928); p. 443 View in Reaxys

OH O

Rx-ID: 645850 View in Reaxys 599/804 Yield

Conditions & References With bacterium ascendens, calcium carbonate, unter aeroben oder anaeroben Bedingungen Neuberg; Windisch; Biochemische Zeitschrift; vol. 166; (1925); p. 471; Naturwissenschaften; vol. 13; p. 994; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 1667 View in Reaxys With bacterium xylinium, calcium carbonate, unter aeroben oder anaeroben Bedingungen Neuberg; Windisch; Biochemische Zeitschrift; vol. 166; (1925); p. 471; Naturwissenschaften; vol. 13; p. 994; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 1667 View in Reaxys

2.2-dimethyl-pentane-dicarboxylic acid-(1.3)

Rx-ID: 6188364 View in Reaxys 600/804 Yield

Conditions & References With sulfuric acid Kon; Smith; Thorpe; Journal of the Chemical Society; vol. 127; (1925); p. 570 View in Reaxys With potassium hydroxide Kon; Smith; Thorpe; Journal of the Chemical Society; vol. 127; (1925); p. 570 View in Reaxys

acetyl-<β-carboxy-propionyl>-peroxide

HO O

Rx-ID: 6188365 View in Reaxys 601/804 Yield

Conditions & References T= 180 °C Brunner; Helvetica Chimica Acta; vol. 8; (1925); p. 653 View in Reaxys

calcium carbonate

HO OH O

Rx-ID: 6208005 View in Reaxys 602/804 Yield

Conditions & References durch Bact.ascendens unter anaeroben und aeroben Bedingungen Neuberg; Windisch; Biochemische Zeitschrift; vol. 166; (1925); p. 471; Naturwissenschaften; vol. 13; p. 994; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 1667 View in Reaxys durch Bact.xylinum unter anaeroben und aeroben Bedingungen

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Neuberg; Windisch; Biochemische Zeitschrift; vol. 166; (1925); p. 471; Naturwissenschaften; vol. 13; p. 994; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 1667 View in Reaxys O

O OH

OH HO

S OO

Rx-ID: 7066048 View in Reaxys 603/804 Yield

Conditions & References Kon; Smith; Thorpe; Journal of the Chemical Society; vol. 127; (1925); p. 570 View in Reaxys

O H

Rx-ID: 156445 View in Reaxys 604/804 Yield

Conditions & References bei der Vergaerung durch Bac.granulobacter pectinovorum Speakman; Journal of Biological Chemistry; vol. 58; (1924); p. 398,400,404 View in Reaxys bei der Aceton-Butylalkohol-Gaerung durch Bac.granulobacter pectinovorum Speakman; Journal of Biological Chemistry; vol. 58; (1924); p. 398,400,404 View in Reaxys

HO O

Rx-ID: 161375 View in Reaxys 605/804 Yield

Conditions & References Oxydation an der Luft Delepine; Bulletin des Societes Chimiques Belges; vol. 33; (1924); p. 339 View in Reaxys Delepine; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 174; (1922); p. 1291; Bulletin de la Societe Chimique de France; vol. <4>31; (1922); p. 762,772 View in Reaxys

OH HO

HO OH O

Rx-ID: 201059 View in Reaxys 606/804 Yield

Conditions & References durch Bacillus granulobacter pectinovorum;Produkt 5:Milchsaeure Speakman; Journal of Biological Chemistry; vol. 58; (1924); p. 398,400,404 View in Reaxys Schmidt; Petrson; Fred; Journal of Biological Chemistry; vol. 61; (1924); p. 163 View in Reaxys

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OH HO

HO O

Rx-ID: 201079 View in Reaxys 607/804 Yield

Conditions & References bei der Aceton-Butylalkohol-Gaerung durch Bac.granulobacter pectinovorum Speakman; Journal of Biological Chemistry; vol. 58; (1924); p. 398,400,404 View in Reaxys bei der Vergaerung durch Bac.granulobacter pectinovorum Speakman; Journal of Biological Chemistry; vol. 58; (1924); p. 398,400,404 View in Reaxys

O H

HO O

Rx-ID: 202425 View in Reaxys 608/804 Yield

HO O

OH OH

Rx-ID: 204389 View in Reaxys 609/804 Yield

starch

HO O

Rx-ID: 6188406 View in Reaxys 610/804

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Yield

Conditions & References bei der Vergaerung durch Bac.granulobacter pectinovorum Speakman; Journal of Biological Chemistry; vol. 58; (1924); p. 398,400,404 View in Reaxys O E

permanganate

O HO

OH O

O O

Rx-ID: 7066177 View in Reaxys 611/804 Yield

Conditions & References Staudinger; Ruzicka; Helvetica Chimica Acta; vol. 7; (1924); p. 255 View in Reaxys

OH O

Rx-ID: 7066690 View in Reaxys 612/804 Yield

Conditions & References bei mehrmonatiger Belichtung mit Sonnenlicht; Produkt5:Ameisensaeure; Produkt5:Ameisensaeure; Produkt6:Dibutylaetherperoxyd Clover; Journal of the American Chemical Society; vol. 46; (1924); p. 423 View in Reaxys

air oxygen

dibutyl ether peroxide

OH O

Rx-ID: 7073810 View in Reaxys 613/804 Yield

Conditions & References T= 70 - 75 °C , bei mehrtaegiger Belichtung; Produkt5:Buttarsaeurebutylester; Produkt6:Ameisensaeure Clover; Journal of the American Chemical Society; vol. 46; (1924); p. 423 View in Reaxys O

OH H OS O

sodium amalgam

alkali

racemate

Rx-ID: 8491148 View in Reaxys 614/804 Yield

Conditions & References Ahlberg; Journal fuer Praktische Chemie (Leipzig); vol. <2> 107; (1924); p. 291; Chemische Berichte; vol. 61; (1928); p. 817 View in Reaxys

γ.γ.γ-trichloro-crotonic acid

Rx-ID: 6188362 View in Reaxys 615/804

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Yield

Conditions & References With sodium amalgam, in neutraler loesung v.Auwers; Wissebach; Chemische Berichte; vol. 56; (1923); p. 737 View in Reaxys

γ.γ-dichloro-crotonic acid

Rx-ID: 6188363 View in Reaxys 616/804 Yield

Conditions & References With sodium amalgam, in neutraler loesung v.Auwers; Wissebach; Chemische Berichte; vol. 56; (1923); p. 737 View in Reaxys Cl

Cl H

sodium amalgam

γ.γ-dichloro-crotonic acid O

Rx-ID: 7066076 View in Reaxys 617/804 Yield

Conditions & References v.Auwers; Wissebach; Chemische Berichte; vol. 56; (1923); p. 737 View in Reaxys

γ.γ-dichloro-crotonic acid

E O

HO O

Rx-ID: 7066091 View in Reaxys 618/804 Yield

Conditions & References With sodium amalgam, water v.Auwers; Chemische Berichte; vol. 56; (1923); p. 730 View in Reaxys O

(v4)

Rx-ID: 7066164 View in Reaxys 619/804 Yield

Conditions & References nachfolgende Zersetzung mit Wasser v.Auwers; Heyna; Justus Liebigs Annalen der Chemie; vol. 434; (1923); p. 158 View in Reaxys

oxygen

manganese stearate

O O

Rx-ID: 6188425 View in Reaxys 620/804 Yield

Conditions & References T= 120 - 130 °C Salway; Williams; Journal of the Chemical Society; vol. 121; (1922); p. 1345

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View in Reaxys

OH OH

chromic acid

O O

OH O

Rx-ID: 7066085 View in Reaxys 621/804 Yield

Conditions & References Asahina; Shimidzu; Yakugaku Zasshi; nb. 479; (1922); p. 2; Chem. Zentralbl.; vol. 93; nb. I; (1922); p. 976 View in Reaxys

potassium permanganate O

KOH-solution

Rx-ID: 7066133 View in Reaxys 622/804 Yield

Conditions & References T= 37 °C Levene; Taylor; Journal of Biological Chemistry; vol. 54; (1922); p. 354 View in Reaxys O O

copper

aluminium oxide

HO O

Rx-ID: 7066174 View in Reaxys 623/804 Yield

Conditions & References T= 550 °C Mailhe; Annales de Chimie (Cachan, France); vol. <9> 17; (1922); p. 308,317; ; vol. 19; p. 11474; Chem. Zentralbl.; vol. 94; nb. III; (1923); p. 38 View in Reaxys O

bacillus butylicus Fitz

calcium carbonate

HO O

Rx-ID: 5714598 View in Reaxys 624/804 Yield

Conditions & References Neuberg; Arinstein; Biochemische Zeitschrift; vol. 117; (1921); p. 298 View in Reaxys

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α-oxo-γ-valerolactone-γ-carboxylic acid

Rx-ID: 6188359 View in Reaxys 625/804 Yield

Conditions & References With calcium carbonate, bei der Vergaerung durch Bacillus butylicus Fitz Neuberg; Arinstein; Biochemische Zeitschrift; vol. 117; (1921); p. 298 View in Reaxys

corn starch

Rx-ID: 6188380 View in Reaxys 626/804 Yield

Conditions & References bei der Aceton-Butylalkohol-Gaerung durch ein als B.Y. bezeichnetes Bacterium Neppi; ; vol. 2; (1920); p. 173 View in Reaxys bei der Aceton-Butylalkohol-Gaerung durch Bac.granulobacter pectinovorum Speakman; Journal of Biological Chemistry; vol. 41; (1920); p. 328; Journal of Biological Chemistry; vol. 58; (1924); p. 398 View in Reaxys bei der Vergaerung durch Granulobacterium butylicum (Beijerinck) Folpmers; ; vol. 6; p. 449; Chem. Zentralbl.; vol. 92; nb. III; (1921); p. 47 View in Reaxys

potatoestarch

Rx-ID: 6188402 View in Reaxys 627/804 Yield

Conditions & References bei der Vergaerung durch Granulobacterium butylicum Folpmers; ; vol. 6; p. 449; Chem. Zentralbl.; vol. 92; nb. III; (1921); p. 47 View in Reaxys With potassium phosphate, water, magnesium sulfate, T= 40 °C , und Salmiak und Calciumcarbonat und Heuinfus ;nach 10-taegigem Stehen werden die entstandenen Calciumsalze mit Salzsaeure zerlegt,die fluechtigen Saeuren abdestilliert und fraktioniert Emmerling; Chemische Berichte; vol. 30; (1897); p. 451 View in Reaxys Buchner; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 9; (1885); p. 398 View in Reaxys

O H HO

OH H

alcohol, butyl alcohol, formic acid and acetic acid O

OH racemate

Rx-ID: 6209494 View in Reaxys 628/804 Yield

Conditions & References bei der Vergaerung durch Bac.butylicus Fitz in anorganischem Medium

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Neuberg; Arinstein; Biochemische Zeitschrift; vol. 117; (1921); p. 298 View in Reaxys O

O –O

Na +

Rx-ID: 45918 View in Reaxys 629/804 Yield

Conditions & References T= 250 °C , analog verlaeuft die Reaktion mit Natriumaethylat und Natriumpropylat Wolff; Thielepape; Justus Liebigs Annalen der Chemie; vol. 420; (1920); p. 283 View in Reaxys O

Rx-ID: 727586 View in Reaxys 630/804 Yield

Conditions & References With sodium methylate, T= 250 °C Wolff; Thielepape; Justus Liebigs Annalen der Chemie; vol. 420; (1920); p. 283 View in Reaxys

Rx-ID: 845512 View in Reaxys 631/804 Yield

Conditions & References With calcium, T= 235 °C Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys With CaO, T= 250 - 260 °C Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys

paraffin

HO O

Rx-ID: 6188399 View in Reaxys 632/804 Yield

Conditions & References With oxygen, T= 150 °C , in Gegenwart von Manganverbindungen Kelber; Chemische Berichte; vol. 53; (1920); p. 70 View in Reaxys With oxygen, T= 150 °C , unter Druck in Gegenwart von Quecksilber-, Blei-, Vanadium-, Chrom- oder Mangan-Verbindungen Franck; Chemiker-Zeitung, Chemische Apparatur; vol. 44; (1920); p. 309; Chem. Zentralbl.; vol. 91; nb. II; (1920); p. 781 View in Reaxys T= 130 - 135 °C Bergmann; Angewandte Chemie; vol. 31; (1918); p. 69 View in Reaxys

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β-ethyl-n-hexyl alcohol and α-ethyl-n-caproic acid

OH O

Rx-ID: 6188409 View in Reaxys 633/804 Yield

Conditions & References With sodium, T= 250 °C , unter Druck Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys With sodium hydroxide, T= 275 °C Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys

calcium (28 percent )

Rx-ID: 6684739 View in Reaxys 634/804 Yield

Conditions & References T= 235 °C Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys

calcium oxide

Rx-ID: 6684740 View in Reaxys 635/804 Yield

Conditions & References T= 250 - 260 °C Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys H OH

sodium (15 percent )

Rx-ID: 6684745 View in Reaxys 636/804 Yield

Conditions & References T= 200 - 275 °C , unter Druck Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys H OH

sodium hydroxide (30-50 percent )

HO O

Rx-ID: 6684746 View in Reaxys 637/804 Yield

Conditions & References T= 275 °C , unter Druck Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys

sodium (5-10 percent )

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H HO

Rx-ID: 6684747 View in Reaxys 638/804 Yield

Conditions & References T= 200 - 275 °C , unter Druck Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys

air

copper

O O

Rx-ID: 6684754 View in Reaxys 639/804 Yield

Conditions & References T= 270 °C Mailhe; de Godon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 517; Bulletin de la Societe Chimique de France; vol. <4> 27; (1920); p. 333 View in Reaxys

copper

O O

Rx-ID: 6684763 View in Reaxys 640/804 Yield

Conditions & References T= 400 °C Weizmann; Garrard; Journal of the Chemical Society; vol. 117; (1920); p. 329 View in Reaxys

HO O

Rx-ID: 8264148 View in Reaxys 641/804 Yield

Conditions & References Hydrolysis Moureu; Mignonac; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 170; (1920); p. 1354; Annales de Chimie (Cachan, France); vol. <9> 14; (1920); p. 341 View in Reaxys

OH H

HO O

Rx-ID: 206148 View in Reaxys 642/804 Yield

Conditions & References bei der Kalischmelze Noorduyn; Recueil des Travaux Chimiques des Pays-Bas; vol. 38; (1919); p. 327 View in Reaxys

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KO H HO

HO O

Z O

Rx-ID: 7066158 View in Reaxys 643/804 Yield

Conditions & References T= 260 - 280 °C , Produkt5: Valeriansaeure Noorduyn; Recueil des Travaux Chimiques des Pays-Bas; vol. 38; (1919); p. 327 View in Reaxys

chromic acid

Rx-ID: 8264140 View in Reaxys 644/804 Yield

Conditions & References Langlois; Annales de Chimie (Cachan, France); vol. <9> 12; (1919); p. 271,337 View in Reaxys

H N

chromium trioxide O HO

hygrinic acid O

Rx-ID: 5735279 View in Reaxys 645/804 Yield

Conditions & References Hess; Eichel; Uibrig; Chemische Berichte; vol. 50; (1917); p. 363 View in Reaxys

glucose-pepton

HO O

Rx-ID: 6188386 View in Reaxys 646/804 Yield

Conditions & References bei der Einw. von Bacillus sporogenes und Bacillus perfringens Wolf; Telfer; Biochemical Journal; vol. 11; (1917); p. 201 View in Reaxys

milk

HO O

Rx-ID: 6188395 View in Reaxys 647/804 Yield

Conditions & References bei der Einw. von Bacillus sporogenes und Bacillus perfringens Wolf; Telfer; Biochemical Journal; vol. 11; (1917); p. 201 View in Reaxys

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potassium persulfate

NH 2

Rx-ID: 6684748 View in Reaxys 648/804 Yield

Conditions & References Datta; Sen; Journal of the American Chemical Society; vol. 39; (1917); p. 749 View in Reaxys

O O

HO O

Rx-ID: 65824 View in Reaxys 649/804 Yield

Conditions & References With water, Geschwindigkeit der Bildung Wilsdon; Sidgwick; Journal of the Chemical Society; vol. 103; (1913); p. 1965 View in Reaxys Verkade; Recueil des Travaux Chimiques des Pays-Bas; vol. 35; (1916); p. 102 View in Reaxys

potassium permanganate

OH O

Rx-ID: 5714605 View in Reaxys 650/804 Yield

Conditions & References Franke; Lieben; Monatshefte fuer Chemie; vol. 35; (1914); p. 1433; Monatshefte fuer Chemie; vol. 43; (1922); p. 227 View in Reaxys

HO O

Rx-ID: 228960 View in Reaxys 651/804 Yield

Conditions & References With potassium permanganate Przewalski; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 897; Journal fuer Praktische Chemie (Leipzig); vol. <2>88; (1913); p. 498 View in Reaxys Przewalski; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 43; (1911); p. 1001; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 895; Chem. Zentralbl.; vol. 82; nb. II; (1911); p. 1914 View in Reaxys

Rx-ID: 850264 View in Reaxys 652/804 Yield

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View in Reaxys O O

platinum black

Cl Cl

lactone of a(n) oxyoic acid O

Rx-ID: 5736563 View in Reaxys 653/804 Yield

Conditions & References Hydrogenation, higher-melting (stable) form Ott; Chemische Berichte; vol. 46; (1913); p. 2173 View in Reaxys

caproic acid of fermentation

Rx-ID: 6188371 View in Reaxys 654/804 Yield

chloromaleic acid chloride

Rx-ID: 6188379 View in Reaxys 655/804 Yield

Conditions & References With hydrogen, platinum Ott; Chemische Berichte; vol. 46; (1913); p. 2173 View in Reaxys

alkaline KMnO4 O

O HO

OH O

Rx-ID: 6208269 View in Reaxys 656/804 Yield

Conditions & References T= 37 °C , und anderes Produkt: Glutarsaeure, caproic acid of fermentation Przewalski; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 43; (1911); p. 1001; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 895; Chem. Zentralbl.; vol. 82; nb. II; (1911); p. 1914 View in Reaxys Przewalski; Journal fuer Praktische Chemie (Leipzig); vol. <2> 88; (1913); p. 496 View in Reaxys O

KMnO4 O

Rx-ID: 6684761 View in Reaxys 657/804

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Yield

Conditions & References und andere Produkt: Oxalsaeure Przewalsky; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 896; Journal fuer Praktische Chemie (Leipzig); vol. <2>88; (1913); p. 498 View in Reaxys

alkaline KMnO4 O

Rx-ID: 7067113 View in Reaxys 658/804 Yield

Conditions & References und andere Produkten: Bernsteinsaeure,Adipinsaeure,Glutarsaeure,Ketosaeure (C7H12O3),Ketosaeure (C7H12O3) und eine Dioxydicarbonsaeure (C7H12O6)? Przewalski; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 43; (1911); p. 1001; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 45; (1913); p. 895; Chem. Zentralbl.; vol. 82; nb. II; (1911); p. 1914 View in Reaxys Przewalski; Journal fuer Praktische Chemie (Leipzig); vol. <2> 88; (1913); p. 496 View in Reaxys

aqueous KOH-solution

Rx-ID: 7066178 View in Reaxys 659/804 Yield

Conditions & References Lespieau; Annales de Chimie (Cachan, France); vol. <8>27; (1912); p. 169; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 879 View in Reaxys

O N

Rx-ID: 8264136 View in Reaxys 660/804 Yield

Conditions & References Schmidt; Sigwart; Chemische Berichte; vol. 45; (1912); p. 1785 View in Reaxys

O O

Rx-ID: 204946 View in Reaxys 661/804 Yield

Conditions & References bei anaeroben Gaerung des Monokaliumtartrats und des Calciumtartrats durch Bakterien Ordonneau; Bulletin de la Societe Chimique de France; vol. <4>9; (1911); p. 400 View in Reaxys

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HO O

Rx-ID: 6188412 View in Reaxys 662/804 Yield

Conditions & References T= 280 - 300 °C , Gleichgewicht der Reaktion in Gegenwart von TiO2 bei 71prozent Ester Sabatier; Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 496 View in Reaxys

HO O

Rx-ID: 7066088 View in Reaxys 663/804 Yield

Conditions & References T= 280 - 300 °C , Gleichgewicht der Reaktion in Gegenwart von TiO2 bei 72.7prozent Ester Sabatier; Mailhe; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 496 View in Reaxys

O O

Rx-ID: 7066104 View in Reaxys 664/804 Yield

Conditions & References mit UV-Strahlen.Irradiation Berthelot; Gaudechon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 262 View in Reaxys

O H

H OH

HO O

Rx-ID: 7066105 View in Reaxys 665/804 Yield

Conditions & References mit UV-Strahlen.Irradiation Berthelot; Gaudechon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 262 View in Reaxys

O H

H OH

uranium salt

HO O

Rx-ID: 7066107 View in Reaxys 666/804 Yield

Conditions & References mit UV-Strahlen oder im Sonnenlicht.Irradiation Seekamp; Justus Liebigs Annalen der Chemie; vol. 133; (1865); p. 253 View in Reaxys

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Berthelot; Gaudechon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 262 View in Reaxys

alkaline KMnO4

oxygen

Rx-ID: 6188398 View in Reaxys 667/804 Yield

Conditions & References Fournier; Bulletin de la Societe Chimique de France; vol. <4>7; (1910); p. 25 View in Reaxys

oxygen

platinum black

Rx-ID: 6188400 View in Reaxys 668/804 Yield

Conditions & References Fournier; Bulletin de la Societe Chimique de France; vol. <4>7; (1910); p. 25 View in Reaxys

O HO

OH O

NH 2

Rx-ID: 203288 View in Reaxys 669/804 Yield

Conditions & References bei der ammoniakalischen Gaerung Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 239; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 1663 View in Reaxys Patent; Effront; DE215531 View in Reaxys Effront; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 548 View in Reaxys

NH 2

OH O

Rx-ID: 203343 View in Reaxys 670/804 Yield

Conditions & References Zers. durch Faeulnisbazillen Brasch; Neuberg; Biochemische Zeitschrift; vol. 13; (1908); p. 299 View in Reaxys Borchardt; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 59; (1909); p. 98 View in Reaxys

NH 2

OH O

O HO

OH O

Rx-ID: 203344 View in Reaxys 671/804 Yield

Conditions & References Zers. durch Faeulnisbazillen Brasch; Biochemische Zeitschrift; vol. 18; (1909); p. 380 View in Reaxys Brasch; Neuberg; Biochemische Zeitschrift; vol. 13; (1908); p. 299

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View in Reaxys O HO OH O

NH 2

Rx-ID: 752298 View in Reaxys 672/804 Yield

Conditions & References durch Bacillus putrificus Brasch; Biochemische Zeitschrift; vol. 22; (1909); p. 408 View in Reaxys bei der Einw. von Bacillus putrificus Brasch; Biochemische Zeitschrift; vol. 22; (1909); p. 408 View in Reaxys

active glutamic acid

Rx-ID: 6188367 View in Reaxys 673/804 Yield

Conditions & References bei der Zersetzung durch Faeulnisbakterien Neuberg; Biochemische Zeitschrift; vol. 18; (1909); p. 431 View in Reaxys Brasch; Biochemische Zeitschrift; vol. 18; (1909); p. 380 View in Reaxys Brasch; Neuberg; Biochemische Zeitschrift; vol. 13; (1908); p. 299 View in Reaxys

distillery-slut

HO O

Rx-ID: 6188383 View in Reaxys 674/804 Yield

Conditions & References With aluminium salt, press-yeast, T= 38 - 43 °C , unter Lueftung ;ammoniakalische Gaerung Effront; Chem. Zentralbl.; vol. 80; nb. II; (1909); p. 1709 View in Reaxys Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 239; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 1663 View in Reaxys Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 146; (1908); p. 780; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 584 View in Reaxys With aluminium salt, garden mold, T= 38 - 43 °C , unter Lueftung ;ammoniakalische Gaerung Effront; Chem. Zentralbl.; vol. 80; nb. II; (1909); p. 1709 View in Reaxys Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 239; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 1663 View in Reaxys Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 146; (1908); p. 780; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 584 View in Reaxys

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inactive glutamic acid

Rx-ID: 6188387 View in Reaxys 675/804 Yield

molasses

Rx-ID: 6188396 View in Reaxys 676/804 Yield

Conditions & References Gaerung erfolgt mit Buttersaeurebacterien bei 35-40grad,Kreide hinzufuegen,nach 8-10 Tagen Calciumcarbonat abfiltrieren,Filtrat eindampfen,Calciumbutyrat mit Schwefelsaeure zersetzen,Buttersaeure destillieren und fraktionieren Szameitat; View in Reaxys With aluminium salt, press-yeast, T= 38 - 43 °C , unter Lueftung ;ammoniakalische Gaerung Effront; Chem. Zentralbl.; vol. 80; nb. II; (1909); p. 1709 View in Reaxys Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 239; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 1663 View in Reaxys Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 146; (1908); p. 780; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 584 View in Reaxys With aluminium salt, garden mold, T= 38 - 43 °C , unter Lueftung ;ammoniakalische Gaerung Effront; Chem. Zentralbl.; vol. 80; nb. II; (1909); p. 1709 View in Reaxys Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 239; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 1663 View in Reaxys Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 146; (1908); p. 780; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 584 View in Reaxys O OH

zinc

HO O

Rx-ID: 6684736 View in Reaxys 677/804 Yield

Conditions & References Kishner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 41; (1909); p. 660; Chem. Zentralbl.; vol. 80; nb. II; (1909); p. 1130 View in Reaxys

hydrogen

nickel

Rx-ID: 7066058 View in Reaxys 678/804

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Yield

Conditions & References T= 190 °C Sabatier; Mailhe; Annales de Chimie (Cachan, France); vol. <8>16; (1909); p. 107 View in Reaxys

NH 2

OH O

Rx-ID: 7066110 View in Reaxys 679/804 Yield

Conditions & References durch Blumenerde oder durch das in ihr enthaltene Buttersaeurebacterium Effront; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 238 View in Reaxys

NH 2

OH O

HO O

Rx-ID: 7066161 View in Reaxys 680/804 Yield

Conditions & References ammoniakalische Gaerung in Gegenwart von Bierhefe Effront; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 1663 View in Reaxys

fats/fatty

Rx-ID: 6188384 View in Reaxys 681/804 Yield

Conditions & References With nitric acid Redtenbacher; Justus Liebigs Annalen der Chemie; vol. 59; (1846); p. 49 View in Reaxys beim Ranzigwerden Scala; Gazzetta Chimica Italiana; vol. 38 I; (1908); p. 312; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 440 View in Reaxys

oils

Rx-ID: 6188397 View in Reaxys 682/804 Yield

Conditions & References beim Ranzigwerden Scala; Gazzetta Chimica Italiana; vol. 38 I; (1908); p. 312; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 440 View in Reaxys

HO O

hydrogen,carbon dioxid,ethanol,n-butyl alcohol,formic acid ,acetic acid ,n-caproic acid ,lactic acid etc. Rx-ID: 6214717 View in Reaxys 683/804

Yield

Conditions & References T= 37 - 40 °C , bei der Buttersaeuregaerung

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Buchner; Meisenheimer; Chemische Berichte; vol. 41; (1908); p. 1411 View in Reaxys Czapek; View in Reaxys Schattenfroh; Grassberger; Chem. Zentralbl.; vol. 71; nb. I; (1900); p. 777 View in Reaxys Schattenfroh; Grassberger; Chem. Zentralbl.; vol. 70; nb. II; (1899); p. 1060 View in Reaxys Schattenfroh; Grassberger; Chem. Zentralbl.; vol. 70; nb. I; (1899); p. 1249 View in Reaxys v.Klecki; Chem. Zentralbl.; vol. 67; nb. II; (1896); p. 253 View in Reaxys Baier; Chem. Zentralbl.; vol. 66; nb. I; (1895); p. 697 View in Reaxys Grimbert; Chem. Zentralbl.; vol. 65; nb. I; (1894); p. 871 View in Reaxys Baginsky; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 12; (1888); p. 462 View in Reaxys Deherain; Maquenne; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 97; (1883); p. 803 View in Reaxys Fitz; Chemische Berichte; vol. 17; (1884); p. 1188 View in Reaxys Fitz; Chemische Berichte; vol. 11; (1878); p. 42; Chemische Berichte; vol. 13; (1880); p. 1309 View in Reaxys Fitz; Chemische Berichte; vol. 9; (1876); p. 1348; Chemische Berichte; vol. 10; (1877); p. 276 View in Reaxys Beijerinck; Chem. Zentralbl.; vol. 68; nb. I; (1897); p. 330 View in Reaxys Emmerling; Chemische Berichte; vol. 29; (1896); p. 2727 View in Reaxys O

OH NH 2

NH 2

OH O

H 2N 2

Rx-ID: 7066169 View in Reaxys 684/804 Yield

Conditions & References anaerob Zerlegung durch den Bacillus proteus vulgaris, l-asparagine Nawiasky; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 340 View in Reaxys O HO

hydrogen peroxide

NH3

CO2

NH 2

Rx-ID: 7082261 View in Reaxys 685/804 Yield

Conditions & References Dakin; Chem. Zentralbl.; vol. 79; nb. I; (1908); p. 1165 View in Reaxys

casein

HO O

Rx-ID: 6188377 View in Reaxys 686/804 Yield

Conditions & References bei der Faeulnis Neuberg; Chem. Zentralbl.; vol. 78; nb. II; (1907); p. 266 View in Reaxys

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Iljenko; Justus Liebigs Annalen der Chemie; vol. 63; (1847); p. 268 View in Reaxys Iljenko; Laskowsky; Justus Liebigs Annalen der Chemie; vol. 55; (1845); p. 85 View in Reaxys

alkaline KMnO4

Rx-ID: 6684730 View in Reaxys 687/804 Yield

Conditions & References Fournier; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 144; (1907); p. 333; Bulletin de la Societe Chimique de France; vol. <4>5; (1909); p. 920 View in Reaxys

chromic acid

acid O

Rx-ID: 7068367 View in Reaxys 688/804 Yield

Conditions & References Saizew,P.u.A.; Journal fuer Praktische Chemie (Leipzig); vol. <2>76; (1907); p. 102 View in Reaxys O

OH HO

S OO

α-p-tolyl-α-butylene O

Rx-ID: 8264143 View in Reaxys 689/804 Yield

Conditions & References Mazurewitsch; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 39; (1907); p. 184,188; Chem. Zentralbl.; vol. 78; nb. II; (1907); p. 146 View in Reaxys

OH HO

azotobacter

Rx-ID: 7066134 View in Reaxys 690/804 Yield

Conditions & References Stoklasa; Chem. Zentralbl.; vol. 77; nb. I; (1906); p. 1036 View in Reaxys O O

CrO3

O HO

HO O

Rx-ID: 7449264 View in Reaxys 691/804 Yield

Conditions & References Layraud; Bulletin de la Societe Chimique de France; vol. <3> 35; (1906); p. 233 View in Reaxys

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β-ethoxycrotonic acid ethyl ester

HO O

Rx-ID: 7066093 View in Reaxys 692/804 Yield

Conditions & References With ethanol, sodium Bouveault; Blanc; Bulletin de la Societe Chimique de France; vol. <3>31; (1904); p. 1210 View in Reaxys

sodium

HO O

Rx-ID: 7066094 View in Reaxys 693/804 Yield

Conditions & References Bouveault; Blanc; Bulletin de la Societe Chimique de France; vol. <3>31; (1904); p. 1210 View in Reaxys

KMnO4

HO O

Rx-ID: 7066147 View in Reaxys 694/804 Yield

Conditions & References Kadiera; Monatshefte fuer Chemie; vol. 25; (1904); p. 332 View in Reaxys

HO O

potassium permanganate

alkali

Rx-ID: 7066173 View in Reaxys 695/804 Yield

Conditions & References Produkt5: Malonsaeure Fittig; Dannenberg; Justus Liebigs Annalen der Chemie; vol. 331; (1904); p. 123 View in Reaxys

O O HO

N O

zinc dust

compound C20H22O6 O

Rx-ID: 5729358 View in Reaxys 696/804 Yield

Conditions & References Boehm; Justus Liebigs Annalen der Chemie; vol. 329; (1903); p. 316,317, 319 View in Reaxys

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brown coal

Rx-ID: 6188368 View in Reaxys 697/804 Yield

Conditions & References bei der trocknen Destillation Rosenthal; ; vol. 16; (1903); p. 221 View in Reaxys

γ-phenyl-δ-octylene

HO O

Rx-ID: 6188429 View in Reaxys 698/804 Yield

Conditions & References With potassium permanganate, benzene Riiber; Chemische Berichte; vol. 36; (1903); p. 1406 View in Reaxys OH

filixic acid HO

Rx-ID: 6684737 View in Reaxys 699/804 Yield

Conditions & References With sodium hydroxide, zinc Boehm; Justus Liebigs Annalen der Chemie; vol. 302; (1898); p. 175; Justus Liebigs Annalen der Chemie; vol. 318; (1901); p. 256 View in Reaxys Boehm; Justus Liebigs Annalen der Chemie; vol. 329; (1903); p. 278 View in Reaxys

carbohydrate

Rx-ID: 7066092 View in Reaxys 700/804 Yield

Conditions & References bei der Vergaerung durch manche Buttersaeurebakterien oder verwandte pathogene Buttersaeuregaerungserreger Schattenfroh; Grassberger; Chem. Zentralbl.; vol. 71; nb. I; (1900); p. 777 View in Reaxys Schattenfroh; Grassberger; Chem. Zentralbl.; vol. 70; nb. I; (1899); p. 1249 View in Reaxys Grassberger; Chem. Zentralbl.; vol. 74; nb. II; (1903); p. 843 View in Reaxys O

O O

O N O

O O

zinc dust

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HO O

Rx-ID: 7449262 View in Reaxys 701/804 Yield

Conditions & References Boehm; Justus Liebigs Annalen der Chemie; vol. 329; (1903); p. 278 View in Reaxys

KMnO4

HO O

Rx-ID: 8264147 View in Reaxys 702/804 Yield

Conditions & References 1-<11-etho-hexen-(12)-yl>-benzene Riiber; Chemische Berichte; vol. 36; (1903); p. 1406 View in Reaxys

PbO2

Pb4+ O–

Rx-ID: 8284650 View in Reaxys 703/804 Yield

Conditions & References Colson; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 136; (1903); p. 676 View in Reaxys

phosphorus

Rx-ID: 7066066 View in Reaxys 704/804 Yield

Conditions & References Morrell; Crofts; Journal of the Chemical Society; vol. 81; (1902); p. 671 View in Reaxys O

O OH

O HO

S OO

Rx-ID: 7066166 View in Reaxys 705/804 Yield

Conditions & References Bongert; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 133; (1901); p. 165 View in Reaxys Bouveault; Bongert; Bulletin de la Societe Chimique de France; vol. <3> 27; (1902); p. 1083,1088, 1089; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 701,703 View in Reaxys

CrO3 OH

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HO O

enanthyloic acid O

Rx-ID: 7075350 View in Reaxys 706/804 Yield

Conditions & References weiter; Produkt 5:CO2; Produkt 6:Essigsaeure Guerbert; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 134; (1902); p. 469; Annales de Chimie (Cachan, France); vol. <7>27; (1902); p. 93 View in Reaxys O O

HO O

O OH

Rx-ID: 136436 View in Reaxys 707/804 Yield

Conditions & References beim Schmelzen mit Kali bei hoher Temperatur Jowett; Journal of the Chemical Society; vol. 79; (1901); p. 1338 View in Reaxys H N

O– Na +

Rx-ID: 333090 View in Reaxys 708/804 Yield

Conditions & References T= 240 - 250 °C , Es entsteht Buttersaeureaethylanilid,welches bei der Verseifung Buttersaeure liefert Nef; Justus Liebigs Annalen der Chemie; vol. 318; (1901); p. 160; American Chemical Journal; vol. 30; (1903); p. 234 Anm. View in Reaxys

O– Na +

Rx-ID: 333498 View in Reaxys 709/804 Yield

Conditions & References Nef; Justus Liebigs Annalen der Chemie; vol. 318; (1901); p. 160; American Chemical Journal; vol. 30; (1903); p. 234 Anm. View in Reaxys

O Z

aqueous KOH-solution

HO O

Rx-ID: 7066125 View in Reaxys 710/804 Yield

Conditions & References Bouveault; Bongert; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 703; Bulletin de la Societe Chimique de France; vol. <3> 27; (1902); p. 1084 View in Reaxys

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O N

zinc

Rx-ID: 7449259 View in Reaxys 711/804 Yield

Conditions & References Boehm; Justus Liebigs Annalen der Chemie; vol. 318; (1901); p. 301; ; vol. 38; (1897); p. 35 View in Reaxys O

O N O

zinc dust O

Rx-ID: 7449261 View in Reaxys 712/804 Yield

Conditions & References Boehm; Justus Liebigs Annalen der Chemie; vol. 318; (1901); p. 301; ; vol. 38; (1897); p. 35 View in Reaxys O

Br O

alkali

Br HO

Rx-ID: 7449263 View in Reaxys 713/804 Yield

Conditions & References Boehm; Justus Liebigs Annalen der Chemie; vol. 318; (1901); p. 301; ; vol. 38; (1897); p. 35 View in Reaxys O

potassium permanganate

HO O

Rx-ID: 7066101 View in Reaxys 714/804 Yield

Conditions & References Ssemenow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 31; (1899); p. 115; Chem. Zentralbl.; vol. 70; nb. I; (1899); p. 1071 View in Reaxys

HO O H

KMnO4

alkali

O HO

OH HO O

Rx-ID: 7449265 View in Reaxys 715/804 Yield

Conditions & References Balbiano; Gazzetta Chimica Italiana; vol. 29 II; (1899); p. 496; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 1 I; (1892); p. 279 View in Reaxys O O

O HO

HO O

Rx-ID: 125481 View in Reaxys 716/804

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Yield

Conditions & References Bei der Aetznatronschmelze Gucci; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 7 I; (1898); p. 215; Gazzetta Chimica Italiana; vol. 28 I; (1898); p. 297 View in Reaxys

O O

Z O

Rx-ID: 206113 View in Reaxys 717/804 Yield

Conditions & References Produkt5: Oenanthsaeure, Produkt6: Azelainsaeure, Produkt7: Sebacinsaeure, Produkt8: Dioxystearinsaeure(?) Scala; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 439 View in Reaxys

fibrin

Rx-ID: 6188385 View in Reaxys 718/804 Yield

Conditions & References durch Streptokokken Wurtz; Justus Liebigs Annalen der Chemie; vol. 52; (1844); p. 291 View in Reaxys Emmerling; Chemische Berichte; vol. 30; (1897); p. 1870; Chemische Berichte; vol. 33; (1900); p. 2478 View in Reaxys

OH HO

bacillus butylicus

nutrient salt

CaCO3

OH O

Rx-ID: 7066689 View in Reaxys 719/804 Yield

Conditions & References Emmerling; Chemische Berichte; vol. 30; (1897); p. 451 View in Reaxys Fitz; Chemische Berichte; vol. 15; (1882); p. 876 View in Reaxys

alkaline permanganate O

HO O

Rx-ID: 6208270 View in Reaxys 720/804

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Yield

Conditions & References Marie; Annales de Chimie (Cachan, France); vol. <7>7; (1896); p. 183; Bulletin de la Societe Chimique de France; vol. <3>15; (1896); p. 508 View in Reaxys

acid

permanganate

HO O

Rx-ID: 7066118 View in Reaxys 721/804 Yield

Conditions & References Semmler; Chemische Berichte; vol. 25; (1892); p. 3517 View in Reaxys Beckmann; Mehrlaender; Justus Liebigs Annalen der Chemie; vol. 289; (1896); p. 381 View in Reaxys Arth; Annales de Chimie (Cachan, France); vol. <6> 7; (1886); p. 440,447 View in Reaxys

potassium ethyl malonate

K+ O–

Rx-ID: 6188401 View in Reaxys 722/804 Yield

Conditions & References Electrolysis.Edukt 1+2 am +Pol und am -Pol eine durch Zuleiten von Kohlensaeure in ihrer Zusammensetzung konstant gehaltene Kaliumcarbonat-Loesung ;Es entsteht der Aethylester v.Miller; Hofer; Chemische Berichte; vol. 28; (1895); p. 2438 View in Reaxys

–O

O K+

potassium ethyl succinate

adipic acid ester O

Rx-ID: 6209482 View in Reaxys 723/804 Yield

Conditions & References Electrolysis.Edukt 1+2 am +Pol und am -Pol eine durch Zuleiten von Kohlensaeure in ihrer Zusammensetzung konstant gehaltene Kaliumcarbonat-Loesung ;Es entsteht der Aethylester v. Miller; Hofer; Chemische Berichte; vol. 28; (1895); p. 2433 View in Reaxys

Cl Al

Cl O

Rx-ID: 6188410 View in Reaxys 724/804 Yield

Conditions & References Zersetzung des Reaktionsprodukts durch Wasser Combes; Bulletin de la Societe Chimique de France; vol. <3> 11; (1894); p. 716 View in Reaxys

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OH HO

bacillus orthobutylicus

OH O

Rx-ID: 7066685 View in Reaxys 725/804 Yield

Conditions & References Grimbert; Chem. Zentralbl.; vol. 65; nb. I; (1894); p. 871 View in Reaxys O

sodium amalgam

HO O

Rx-ID: 7066078 View in Reaxys 726/804 Yield

Conditions & References in saurer Loesung Michael; Journal fuer Praktische Chemie (Leipzig); vol. <2>46; (1892); p. 266 View in Reaxys Michael; Pendleton; Journal fuer Praktische Chemie (Leipzig); vol. <2> 38; (1888); p. 4 View in Reaxys O

S OO

dichromate

HO O

Rx-ID: 7066140 View in Reaxys 727/804 Yield

Conditions & References Hecht; Justus Liebigs Annalen der Chemie; vol. 269; (1892); p. 321 View in Reaxys O HO

OH O

Rx-ID: 202184 View in Reaxys 728/804 Yield

Conditions & References With uranium oxide nitrate, water, Irradiation.an der Sonne Seekamp; Justus Liebigs Annalen der Chemie; vol. 133; (1865); p. 253 View in Reaxys Wisbar; Justus Liebigs Annalen der Chemie; vol. 262; (1891); p. 235 View in Reaxys

O O

alcohol. KOH-solution

O HO

Rx-ID: 7066081 View in Reaxys 729/804 Yield

Conditions & References Klinger; Schmitz; Chemische Berichte; vol. 24; (1891); p. 1274 View in Reaxys

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NH 2

OH O

Rx-ID: 7066111 View in Reaxys 730/804 Yield

Conditions & References T= 220 °C Kwisda; Monatshefte fuer Chemie; vol. 12; (1891); p. 428 View in Reaxys

HO O

acetate O

Rx-ID: 7068181 View in Reaxys 731/804 Yield

Conditions & References bei der Oxydation Wagner; Journal fuer Praktische Chemie (Leipzig); vol. <2>44; (1891); p. 261 Anm. View in Reaxys

Rx-ID: 224089 View in Reaxys 732/804 Yield

Conditions & References With methanol, sodium Aronstein; Hollemann; Chemische Berichte; vol. 22; (1889); p. 1182 View in Reaxys

sodium amalgam

Rx-ID: 7066070 View in Reaxys 733/804 Yield

Conditions & References Baeyer; Justus Liebigs Annalen der Chemie; vol. 251; (1889); p. 266 View in Reaxys Bulk; Justus Liebigs Annalen der Chemie; vol. 139; (1866); p. 66 View in Reaxys

sodium

Rx-ID: 7066073 View in Reaxys 734/804 Yield

Conditions & References Aronstein; Holleman; Chemische Berichte; vol. 22; (1889); p. 1183 View in Reaxys

chromic acid mixture

Rx-ID: 7066157 View in Reaxys 735/804 Yield

Conditions & References Sokolow; Journal fuer Praktische Chemie (Leipzig); vol. <2>39; (1889); p. 432 View in Reaxys

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N O

alcoholic potash

O O

carbon dioxide // alcohol O

Rx-ID: 7070856 View in Reaxys 736/804 Yield

Conditions & References Kochen Held; Annales de Chimie (Cachan, France); vol. <6> 18; (1889); p. 477; Bulletin de la Societe Chimique de France; vol. <3> 1; (1889); p. 308 View in Reaxys

bacterium lactis aerogenes OH

Rx-ID: 6684733 View in Reaxys 737/804 Yield

Conditions & References Reaktion des Salzes Baginsky; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 12; (1888); p. 448 View in Reaxys

alkaline permanganate O

HO O

Rx-ID: 6188435 View in Reaxys 738/804 Yield

Conditions & References weitere Produkte: Bernsteinsaeure, Adipinsaeure und Dioxypalmitinsaeure(?) Groeger; Monatshefte fuer Chemie; vol. 8; (1887); p. 490,497 View in Reaxys

Cl H

Ag2O

HO O

Rx-ID: 7066050 View in Reaxys 739/804 Yield

Conditions & References Spring; Lecrenier; Bulletin de la Societe Chimique de France; vol. <2>48; (1887); p. 629 View in Reaxys Cl

Cl Cl

Ag2O

HO O

Rx-ID: 7066051 View in Reaxys 740/804 Yield

Conditions & References Spring; Lecrenier; Bulletin de la Societe Chimique de France; vol. <2>48; (1887); p. 629 View in Reaxys

Cl Cl

Ag2O

HO O

Rx-ID: 7066106 View in Reaxys 741/804

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Yield

Conditions & References Spring; Lecrenier; Bulletin de la Societe Chimique de France; vol. <2>48; (1887); p. 629 View in Reaxys

silver

xeronic acid anhydride O

Rx-ID: 7089246 View in Reaxys 742/804 Yield

Conditions & References Otto; Justus Liebigs Annalen der Chemie; vol. 239; (1887); p. 279 View in Reaxys OH

KOH-solution

Rx-ID: 8264137 View in Reaxys 743/804 Yield

Conditions & References T= 160 °C Combes; Annales de Chimie (Cachan, France); vol. <6> 12; (1887); p. 263; Bulletin de la Societe Chimique de France; vol. <3> 11; (1894); p. 710 View in Reaxys

O HO

sodium amalgam

Rx-ID: 7066071 View in Reaxys 744/804 Yield

Conditions & References isomer(ic) I Melikow; Justus Liebigs Annalen der Chemie; vol. 234; (1886); p. 207; Journal fuer Praktische Chemie (Leipzig); vol. <2>61; (1900); p. 557 View in Reaxys

KO H

NH 2 O

HO O

Rx-ID: 7066142 View in Reaxys 745/804 Yield

Conditions & References T= 100 °C Isbert; Justus Liebigs Annalen der Chemie; vol. 234; (1886); p. 170 View in Reaxys

chromic acid mixture OH

Rx-ID: 7066144 View in Reaxys 746/804 Yield

Conditions & References dann Ustinow; Saizew,A.; Journal fuer Praktische Chemie (Leipzig); vol. <2>34; (1886); p. 469 View in Reaxys

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chromic acid mixture

HO O

Rx-ID: 7066159 View in Reaxys 747/804 Yield

Conditions & References Gortalow; Saizew; Journal fuer Praktische Chemie (Leipzig); vol. <2>33; (1886); p. 205 View in Reaxys HO

chromic acid mixture

HO O

Rx-ID: 7066160 View in Reaxys 748/804 Yield

Conditions & References Produkt 5:Butyron Tschebotarew; Saizew; Journal fuer Praktische Chemie (Leipzig); vol. <2>33; (1886); p. 199 View in Reaxys O

concentrated alcoholic KOH-solution

Rx-ID: 7920366 View in Reaxys 749/804 Yield

Conditions & References Baeyer; Perkin; Chemische Berichte; vol. 16; (1883); p. 2130 View in Reaxys Perkin; Journal of the Chemical Society; vol. 45; (1884); p. 178 View in Reaxys

chromic acid mixture

HO O

Rx-ID: 7066156 View in Reaxys 750/804 Yield

Conditions & References Reformatski; Journal fuer Praktische Chemie (Leipzig); vol. <2> 27; (1883); p. 389 View in Reaxys

O O

potassium hydroxide N

OH O

H 2N 2

H 2N

HO O

Rx-ID: 5714607 View in Reaxys 751/804 Yield

Conditions & References beim Schmelzen Chastaing; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 94; (1882); p. 224 View in Reaxys

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bacillus butylicus

OH OH

HO OH

Rx-ID: 6208021 View in Reaxys 752/804 Yield

Conditions & References Fitz; Chemische Berichte; vol. 15; (1882); p. 876 View in Reaxys

HO O

Rx-ID: 646919 View in Reaxys 753/804 Yield

Conditions & References With CaO, T= 250 - 280 °C Ljubawin; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 12; (1880); p. 135 View in Reaxys With sodium, ethyl iodide, Es entsteht der Aethylacetessigester Frankland; Duppa; Justus Liebigs Annalen der Chemie; vol. 138; (1866); p. 218 View in Reaxys Geuther; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1868); p. 514 View in Reaxys Wislicenus,J.; Justus Liebigs Annalen der Chemie; vol. 186; (1877); p. 201,208 View in Reaxys

–O

O– Na +

O Na +

carbon monoxide

Rx-ID: 6188376 View in Reaxys 754/804 Yield

Conditions & References T= 205 °C Geuther; Froelich; Justus Liebigs Annalen der Chemie; vol. 202; (1880); p. 304 View in Reaxys

quicklime

Rx-ID: 6188405 View in Reaxys 755/804 Yield

Conditions & References T= 250 - 280 °C Ljubawin; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 12; (1880); p. 135 View in Reaxys H

2 2

sulfuric acid OH

water O

CaCl 2

Rx-ID: 8428231 View in Reaxys 756/804 Yield

Conditions & References Lieben; Monatshefte fuer Chemie; vol. 1; (1880); p. 926 View in Reaxys

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Rx-ID: 101729 View in Reaxys 757/804 Yield

Conditions & References With potassium hydroxide Hoppe-Seyler; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 2; (1878); p. 14; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 3; (1879); p. 351 View in Reaxys With calcium, durch Buttersaeuregaerung ;nach Zusatz von Fleisch oder Kaese zu der Gaerfluessigkeit unter Zusatz von Kreide beim Stehenlassen mehrerer Wochen bei 25-30grad Pribram; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1879); p. 614 View in Reaxys Grillone; Justus Liebigs Annalen der Chemie; vol. 165; (1873); p. 127 View in Reaxys Bensch; Justus Liebigs Annalen der Chemie; vol. 61; (1847); p. 177 View in Reaxys

carbohydrates

HO O

Rx-ID: 6188372 View in Reaxys 758/804 Yield

Conditions & References durch Buttersaeuregaerung Pribram; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1879); p. 614 View in Reaxys Grillone; Justus Liebigs Annalen der Chemie; vol. 165; (1873); p. 127 View in Reaxys Bensch; Justus Liebigs Annalen der Chemie; vol. 61; (1847); p. 177 View in Reaxys durch Buttersaeuregaerung ;nach Zusatz von Fleisch oder Kaese zu der Gaerfluessigkeit unter Zusatz von Kreide beim Stehenlassen mehrerer Wochen bei 25-30grad Pribram; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1879); p. 614 View in Reaxys Grillone; Justus Liebigs Annalen der Chemie; vol. 165; (1873); p. 127 View in Reaxys Bensch; Justus Liebigs Annalen der Chemie; vol. 61; (1847); p. 177 View in Reaxys

lactate of calcium

HO O

Rx-ID: 6188388 View in Reaxys 759/804 Yield

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OH OH

CaCO3

fission fungi

OH O

Rx-ID: 7066136 View in Reaxys 760/804 Yield

Conditions & References Fitz; Chemische Berichte; vol. 12; (1879); p. 474; Chemische Berichte; vol. 16; (1883); p. 844 View in Reaxys

chromic acid mixture

HO O

Rx-ID: 7066152 View in Reaxys 761/804 Yield

Conditions & References Saizew,P.; Saizew,A.; Justus Liebigs Annalen der Chemie; vol. 196; (1879); p. 109 View in Reaxys

OH H

HO O

OH OH

Rx-ID: 201143 View in Reaxys 762/804 Yield

Conditions & References bei einer Schizomyceten-Gaerung Fitz; Chemische Berichte; vol. 11; (1878); p. 42; Chemische Berichte; vol. 13; (1880); p. 1309 View in Reaxys

OH OH

HO O

Rx-ID: 746534 View in Reaxys 763/804 Yield

Conditions & References With potassium hydroxide Herter; Chemische Berichte; vol. 11; (1878); p. 1167 View in Reaxys

milk acidic lime/chalk/

HO O

Rx-ID: 6188394 View in Reaxys 764/804 Yield

Conditions & References With soda lime Hoppe-Seyler; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 2; (1878); p. 14; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 3; (1879); p. 351 View in Reaxys

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wood

Rx-ID: 6188408 View in Reaxys 765/804 Yield

Conditions & References bei der trocknen Destillation Barre; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1869); p. 515 View in Reaxys Anderson; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1866); p. 310 View in Reaxys Kraemer; Grodzki; Chemische Berichte; vol. 11; (1878); p. 1359 View in Reaxys

alcohol. potash

HO O

Rx-ID: 6188427 View in Reaxys 766/804 Yield

Conditions & References Wislicenus,J.; Justus Liebigs Annalen der Chemie; vol. 190; (1878); p. 262,272 View in Reaxys

chromic acid mixture

HO O

Rx-ID: 7066138 View in Reaxys 767/804 Yield

Conditions & References Hecht; Chemische Berichte; vol. 11; (1878); p. 1423 View in Reaxys

chromic acid

HO O

Rx-ID: 7066139 View in Reaxys 768/804 Yield

Conditions & References Hecht; Munier; Chemische Berichte; vol. 11; (1878); p. 1154 View in Reaxys OH OH

fission fungi

CaCO3

OH O HO

OH O

Rx-ID: 7066176 View in Reaxys 769/804 Yield

Conditions & References Fitz; Chemische Berichte; vol. 11; (1878); p. 1898; Chemische Berichte; vol. 12; (1879); p. 479 View in Reaxys

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OH HO

CaCO3

schizomycetes

ammonium sulfate

phosphate

HO OH

Rx-ID: 7066687 View in Reaxys 770/804 Yield

Conditions & References Produkt5:Essigsaeure; Produkt6:Capronsaeure; Produkt7:Bernsteinsaeure Fitz; Chemische Berichte; vol. 11; (1878); p. 42; Chemische Berichte; vol. 13; (1880); p. 1309 View in Reaxys

HO O

Rx-ID: 257761 View in Reaxys 771/804 Yield

Conditions & References wird von Oxydationsmitteln sehr schwer angegriffen Hercz; Justus Liebigs Annalen der Chemie; vol. 186; (1877); p. 261 View in Reaxys O O

concentrated KOH-solution

OH H

HO O

Rx-ID: 5714602 View in Reaxys 772/804 Yield

Conditions & References Demarcay; Bulletin de la Societe Chimique de France; vol. <2> 27; (1877); p. 484; Annales de Chimie (Cachan, France); vol. <5> 20; (1880); p. 439,465 View in Reaxys

chromic acid O

Rx-ID: 7066145 View in Reaxys 773/804

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Yield

Conditions & References Kurtz; Justus Liebigs Annalen der Chemie; vol. 161; (1872); p. 208 View in Reaxys Hercz; Justus Liebigs Annalen der Chemie; vol. 186; (1877); p. 261 View in Reaxys O

OH O

H 2N 2

Rx-ID: 795837 View in Reaxys 774/804 Yield

Conditions & References T= 160 °C , Zerstzung Markownikow; Justus Liebigs Annalen der Chemie; vol. 182; (1876); p. 328 View in Reaxys Wislicenus; Urech; Justus Liebigs Annalen der Chemie; vol. 165; (1873); p. 95 View in Reaxys

O O

OH O

H 2N 2

HO O

Rx-ID: 6188430 View in Reaxys 775/804 Yield

Conditions & References T= 350 °C , im geschlossenen Rohr Markownikow; Justus Liebigs Annalen der Chemie; vol. 182; (1876); p. 328 View in Reaxys

KMnO4

OH O

Rx-ID: 7066098 View in Reaxys 776/804 Yield

Conditions & References Wurtz; Justus Liebigs Annalen der Chemie; vol. 148; (1868); p. 132 View in Reaxys Wagner; Saizew; Justus Liebigs Annalen der Chemie; vol. 179; (1875); p. 304 View in Reaxys Wurtz; Justus Liebigs Annalen der Chemie; vol. 123; (1862); p. 203; Justus Liebigs Annalen der Chemie; vol. 127; (1863); p. 55 View in Reaxys

calcium salt of/the/ butyric acid

Rx-ID: 6188370 View in Reaxys 777/804 Yield

Conditions & References With sodium carbonate, Zerlegen des Natriumsalzes mit Schwefelsaeure Grillone; Justus Liebigs Annalen der Chemie; vol. 165; (1873); p. 127 View in Reaxys

O E

potash

Rx-ID: 7066131 View in Reaxys 778/804 Yield

Conditions & References beim Schmelzen

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Petriew; Chemische Berichte; vol. 6; (1873); p. 1098 View in Reaxys Frankland; Duppa; Justus Liebigs Annalen der Chemie; vol. 136; (1865); p. 2,18 View in Reaxys

potassium hydroxide

HO O

Rx-ID: 7066132 View in Reaxys 779/804 Yield

Conditions & References Kachel; Fittig; Justus Liebigs Annalen der Chemie; vol. 168; (1873); p. 287 View in Reaxys

HO OH

Rx-ID: 65825 View in Reaxys 780/804 Yield

Conditions & References With sodium amalgam Linnemann; Justus Liebigs Annalen der Chemie; vol. 161; (1872); p. 193 View in Reaxys

H N

O N

Rx-ID: 5714596 View in Reaxys 781/804 Yield

Conditions & References Gruenzweig; Justus Liebigs Annalen der Chemie; vol. 162; (1872); p. 218 View in Reaxys Blyth; Justus Liebigs Annalen der Chemie; vol. 70; (1849); p. 89 View in Reaxys

H N

bromine water

Rx-ID: 5714597 View in Reaxys 782/804 Yield

Conditions & References Gruenzweig; Justus Liebigs Annalen der Chemie; vol. 162; (1872); p. 218 View in Reaxys Blyth; Justus Liebigs Annalen der Chemie; vol. 70; (1849); p. 89 View in Reaxys

H N

chromic acid

HO O

Rx-ID: 5714599 View in Reaxys 783/804 Yield

Conditions & References Gruenzweig; Justus Liebigs Annalen der Chemie; vol. 162; (1872); p. 218 View in Reaxys Blyth; Justus Liebigs Annalen der Chemie; vol. 70; (1849); p. 89 View in Reaxys

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chromic acid-mixture

O O

Rx-ID: 6684752 View in Reaxys 784/804 Yield

Conditions & References Saizew; Journal fuer Praktische Chemie (Leipzig); vol. <2>3; (1871); p. 88 View in Reaxys

chromic acid

Rx-ID: 7066126 View in Reaxys 785/804 Yield

Conditions & References Erlenmeyer; Wanklyn; Justus Liebigs Annalen der Chemie; vol. 135; (1865); p. 141 View in Reaxys O

uranium oxide

OH O

H 2N 2

HO O

Rx-ID: 7066168 View in Reaxys 786/804 Yield

Conditions & References im Sonnenlicht Seekamp; Justus Liebigs Annalen der Chemie; vol. 133; (1865); p. 253 View in Reaxys

OH H

calcium carbonate

white cheese

OH OH

Rx-ID: 7066087 View in Reaxys 787/804 Yield

Conditions & References Berthelot; Annales de Chimie (Cachan, France); vol. <3>50; (1857); p. 348 View in Reaxys OH

HO HO

brewer's yeast

O O

hydrogen O

Rx-ID: 6214894 View in Reaxys 788/804 Yield

Conditions & References das citronensaures Calcium reagiert Personne; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1853); p. 414 View in Reaxys H N

HO O

Rx-ID: 803986 View in Reaxys 789/804

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Yield

Conditions & References With potassium dichromate, sulfuric acid Blyth; Justus Liebigs Annalen der Chemie; vol. 70; (1849); p. 89 View in Reaxys

protein substances

Rx-ID: 6188404 View in Reaxys 790/804 Yield

Conditions & References With manganese(IV) oxide, sulfuric acid Guckelberger; Justus Liebigs Annalen der Chemie; vol. 64; (1847); p. 68,81 View in Reaxys With chromic acid Guckelberger; Justus Liebigs Annalen der Chemie; vol. 64; (1847); p. 68,81 View in Reaxys

HO O

Rx-ID: 60769 View in Reaxys 791/804 Yield

Conditions & References T= 60 °C Kutz; Adkins; Journal of the American Chemical Society; 52<193>4040 View in Reaxys

HO O

OH O OH

Rx-ID: 828799 View in Reaxys 792/804 Yield

HO O

Rx-ID: 845514 View in Reaxys 793/804 Yield

Conditions & References With potassium hydroxide, fired clay gel, T= 280 °C , unter Druck Patent; I.G.Farbenind.; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys With potassium hydroxide, magnesium oxide, T= 280 °C , unter Druck Patent; I.G.Farbenind.; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys Patent; I.G.Farbenind; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys

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With aluminum oxide, potassium hydroxide, T= 280 °C , unter Druck Patent; I.G.Farbenind; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys

O O

potassium hydroxide N

H 2N

Rx-ID: 5714606 View in Reaxys 794/804 Yield

Conditions & References beim Schmelzen Jowett; Proceedings of the Chemical Society, London; vol. 20; p. 14 View in Reaxys

carbohydrate

Rx-ID: 6188373 View in Reaxys 795/804 Yield

Conditions & References bei der Vergaerung durch eine Mischkultur von Bac.butyricus und Bac.putrificus Patent; Lefranc and Cie.; DE478116; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 247 View in Reaxys

starch

malt

Rx-ID: 6188407 View in Reaxys 796/804 Yield

Conditions & References T= 57 - 60 °C , Gaerung erfolgt mit Buttersaeurebacterien bei 35-40grad,Kreide hinzufuegen,nach 8-10 Tagen Calciumcarbonat abfiltrieren,Filtrat eindampfen,Calciumbutyrat mit Schwefelsaeure zersetzen,Buttersaeure destillieren und fraktionieren Szameitat; View in Reaxys

sodium

copper-powder

Rx-ID: 6188434 View in Reaxys 797/804 Yield

Conditions & References T= 280 °C Weizmann; Bergmann; Haskelberg; Chemistry and Industry (London, United Kingdom) View in Reaxys

potassium hydroxide

aluminium oxide gel

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H HO

Rx-ID: 6684743 View in Reaxys 798/804 Yield

Conditions & References T= 280 °C , unter Druck Patent; I.G.Farbenind.; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys

potassium hydroxide

magnesium oxide

H HO

Rx-ID: 6684744 View in Reaxys 799/804 Yield

Conditions & References T= 280 °C , unter Druck Patent; I.G.Farbenind.; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys

potassium hydroxide

aluminium oxide gel

H HO

Rx-ID: 6711833 View in Reaxys 800/804 Yield

Conditions & References T= 400 °C , unter Druck Patent; I.G.Farbenind.; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys T= 550 °C , unter Druck Patent; I.G.Farbenind.; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys

potassium hydroxide

magnesium oxide

H HO

Rx-ID: 6711834 View in Reaxys 801/804 Yield

Conditions & References T= 550 °C , unter Druck Patent; I.G.Farbenind.; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys T= 400 °C , unter Druck Patent; I.G.Farbenind.; DE503009; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 251 View in Reaxys

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Cr2O3-H2SO4 O

HO O

Rx-ID: 7066146 View in Reaxys 802/804 Yield

Conditions & References Pringsheim; Schreiber; ; vol. 8; p. 63 View in Reaxys

OH (v4)

valeric acid (?) O

Rx-ID: 7089119 View in Reaxys 803/804 Yield

Conditions & References Rupe; Hirschmann; Helvetica Chimica Acta; vol. 17; p. 104 View in Reaxys O OH

(v4)

valeric acid (?) O

Rx-ID: 7089120 View in Reaxys 804/804 Yield

Conditions & References Rupe; Hirschmann; Helvetica Chimica Acta; vol. 17; p. 104 View in Reaxys

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